1-Bromo-2-butanone → N-(2-Ethyl imidazo[1,2-a]pyrid-7-yl)-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1944006Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:14]3=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=[C:13]3[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.Br[CH2:33][C:34](=O)[CH2:35][CH3:36]>C(#N)C>[CH2:35]([C:34]1[N:1]=[C:2]2[CH:7]=[C:6]([NH:8][C:9]([C:11]3[N:23]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=4)[C:14]4=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:18]=[C:13]4[CH:12]=3)=[O:10])[CH:5]=[CH:4][N:3]2[CH:33]=1)[CH3:36]

Participants

Conditions

Temperature: 150 °C

Procedure

0.125 g (0.29 mmol) of N-[2-aminopyrid-4-yl]-5-trifluoromethyl-1-[(3-fluorophenyl)-methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide, prepared according to the protocol described in step 15.2, 0.088 g (0.58 mmol) of 1-bromobutan-2-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. 0.076 g of the expected product is thus obtained in the form of a yellow 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-b334977f791f4576ab89b0cd955b8514
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394820B2

Reaction notes

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