2-Bromopropiophenone → N-(3-Methyl-2-phenylimidazo[1,2-a]pyrid-6-yl)-5-fluoro-1-[(3-fluorophenyl)-methyl]-1H-indole-2-carboxamide

HRID 1943990Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([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:4][CH: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:7]2[CH:6]=[C:5]([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:4]=[CH:3][C:2]2=[N:1][C:31]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.05 g (0.13 mmol) of N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide prepared according to the protocol described in step 4.2, 0.056 g (0.26 mmol) of 2-bromo-1-phenylpropan-1-one and 4 mL of acetonitrile are introduced into a 10 mL screw-topped tube equipped with a magnetic bar. The top is then screwed on and the tube is heated at 80° C. with stirring for 24 hours. After this time and cooling to room temperature, the precipitate obtained is filtered off and rinsed successively with 2 mL of acetonitrile and 2 mL of isopropyl ether. The solid obtained is dried under reduced pressure. 0.024 g of the expected product is thus obtained.

Workup

additionare introduced into a 10 mL screw-topped tube
customequipped with a magnetic bar
temperatureAfter this time and cooling to room temperature
customthe precipitate obtained
filtrationis filtered off
washrinsed successively with 2 mL of acetonitrile and 2 mL of isopropyl ether
customThe solid obtained
customis dried under reduced pressure

Sources & evidence

ORD record: ord-c2867a5e2ea94524ab5966f9db86f0bf
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394820B2

Reaction notes

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