Bifluoro C2-spirindoline compound and preparing method thereof
A compound, difluorinated technology, applied in the field of medicine and chemical industry, to achieve the effect of excellent yield, good compatibility, cheap and easy-to-obtain raw materials
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Embodiment 1
[0026] The synthesis of difluoro C2-spiro ring indoline compound shown in formula I-1, reaction formula is as follows:
[0027]
[0028] Add 3,3-difluoro-2-(phenylethynyl)-3H-indole II-1 (57.0mg, 0.225mmol) and benzo[d]thiazol-2-amine II-1 in sequence in a 5mL reaction flask (22.5mg, 0.15mmol), catalyst 1,5,7-triazidebicyclo(4.4.0)dec-5-ene (TBD, 10.5mg, 0.075mmol) and ethyl acetate (1.0mL), the reaction solution Stir at room temperature for 5h. TLC detects that the raw materials have basically reacted, and the reaction is stopped. The reaction solution was subjected to direct column chromatography, eluent (ethyl acetate / dichloromethane=1 / 10), to obtain product I-1 (50.7 mg) in the form of yellow foam, with a yield of 84%.
[0029] The analytical data of difluoro C2-spirocyclic indoline compound shown in formula I-1: 1 H NMR (500MHz, CDCl 3 ):δ4.52(s,1H),5.28(d,J=5Hz,1H),5.89(d,J=10Hz,1H),6.74(d,J=5Hz,1H),6.83(t,J =10Hz,1H),6.93(t,J=5Hz,1H),7.01(t,J=5Hz,1H), 7.31-7.34(...
Embodiment 2
[0031] The synthesis of difluorinated C2 spiroindoline compound shown in formula I-2, reaction formula is as follows:
[0032]
[0033] Add 5-methoxy-3,3-difluoro-2-(p-phenylethynyl)-3H-indole II-2 (63.6mg, 0.225mmol), benzo[d]thiazole in sequence in a 5mL reaction flask -2-Amine III-1 (22.5mg, 0.15mmol), catalyst triethylamine (3.1mg, 0.03mmol) and acetonitrile (2.0mL), the reaction solution was stirred at room temperature for 5h. TLC detects that the raw materials have basically reacted, and the reaction is stopped. The reaction solution was subjected to direct column chromatography, eluent (ethyl acetate / dichloromethane = 1 / 11), to obtain product I-2 (56.5 mg) in the form of yellow foam, with a yield of 87%.
[0034] The analytical data of difluorinated C2 spiroindoline compound shown in formula I-2: 1 H NMR (500MHz, CDCl 3 ):δ3.73(s,3H),4.51(s,1H),5.22(d,J=2.4Hz,1H); 5.77(d,J=10Hz,1H), 6.39(dd,J=10,5.0 Hz,1H),6.73(d,J=10Hz,1H),6.89(d,J=2.6Hz,1H),6.92(t,J=10Hz,1H),7.32...
Embodiment 3
[0036] The synthesis of difluoro C2-spiro ring indoline compound shown in formula I-3, reaction formula is as follows:
[0037]
[0038] Add 3,3-difluoro-2-(p-phenylethynyl)-3H-indole II-3 (61.0 mg, 0.225 mmol), benzo[d]thiazol-2-amine III- 1 (22.5mg, 0.15mmol), catalyst pentamethylpiperidine (PMP, 17.9mg, 0.045mmol) and toluene (5.0mL), the reaction solution was stirred at room temperature for 5h. TLC detected that the raw material had basically reacted, and the reaction was stopped. The reaction solution was subjected to direct column chromatography, eluent (ethyl acetate / dichloromethane=1 / 12), to obtain the product I-3 (45.5 mg) as a yellow solid, with a yield of 72%.
[0039] The analytical data of difluorinated C2 spiroindoline compound shown in formula I-3: 1 H NMR (500MHz, CDCl 3 ): δ4.51(s,1H),5.25(d,J=1.9Hz,1H),5.92(d,J=5Hz,1H),6.74(d,J=10Hz,1H),6.87(td,J =10,1.5Hz,1H),6.93(t,J=10Hz,1H),7.03(t,J=10Hz,1H),7.10-7.19(m,2H),7.31-7.35(m,4H),7.49 (d,J=10Hz,1H); 13 ...
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