2-Bromopropiophenone → N-(2-Methyl-3-phenylimidazo[1,2-a]pyrid-7-yl)-5-fluoro-1-[(3-fluorophenyl)-methyl]-1H-indole-2-carboxamide

HRID 1944001Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([F:20])=[CH:15][CH:14]=3)=[O:10])[CH:5]=[CH:4][N:3]=1.Br[CH:30]([CH3:39])[C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=O>C(#N)C>[CH3:39][C:30]1[N:1]=[C:2]2[CH:7]=[C:6]([NH:8][C:9]([C:11]3[N:12]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([F:20])=[CH:15][CH:14]=4)=[O:10])[CH:5]=[CH:4][N:3]2[C:31]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 150 °C

Procedure

0.1 g (0.26 mmol) of N-[2-aminopyrid-4-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 10.1, 0.11 g (0.53 mmol) of 2-bromo-1-phenylpropan-1-one and 4 mL of acetonitrile are placed in a 10 mL pressure tube specific for microwave reactors. The tube is then sealed and heated in the microwave reactor at 150° C. for two 1-hour cycles. After this time, the reaction mixture is concentrated under reduced pressure. The crude reaction product is then purified by chromatography on a column of silica gel, eluting with a mixture of dichloromethane and methanol. 0.03 g of the expected product is thus obtained in the form of a beige-coloured solid.

Workup

customare placed in a 10 mL pressure tube
customThe tube is then sealed
concentrationAfter this time, the reaction mixture is concentrated under reduced pressure
customThe crude reaction product
customis then purified by chromatography on a column of silica gel
washeluting with a mixture of dichloromethane and methanol

Sources & evidence

ORD record: ord-2072b309d934475d93dbde22a34c320d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394820B2

Reaction notes

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