2-Bromo-6-fluoroaniline → 2-amino-N-(2-bromo-6-fluorophenyl)-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridine-3-carboxamide

HRID 908372Notes

Reaction equation

C[Al](C)C.[Br:5][C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:7]=1[NH2:8].[NH2:14][C:15]1[C:20]([C:21](OC)=[O:22])=[CH:19][C:18]([C:25]2[CH:26]=[N:27][N:28]([CH:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[CH:29]=2)=[CH:17][N:16]=1>C1(C)C=CC=CC=1>[NH2:14][C:15]1[C:20]([C:21]([NH:8][C:7]2[C:9]([F:13])=[CH:10][CH:11]=[CH:12][C:6]=2[Br:5])=[O:22])=[CH:19][C:18]([C:25]2[CH:26]=[N:27][N:28]([CH:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[CH:29]=2)=[CH:17][N:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2M Trimethylaluminium in toluene (0.75 ml) was added to a solution of 2-bromo-6-fluoro-aniline (0.229 g) in toluene (30 ml). The mixture was stirred for 30 minutes, then methyl 2-amino-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridine-3-carboxylate (0.19 g) was added. The mixture was heated to 120° C. for 18 hours, allowed to cool and then quenched with 10% aqueous Rochelle's salt solution. The organic fraction was purified by SCX ion-exchange chromatography to give crude 2-amino-N-(2-bromo-6-fluorophenyl)-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridine-3-carboxamide; Mass Spectrum: M+H+ 472.1; RT 0.87 min.

Workup

temperatureto cool
customquenched with 10% aqueous Rochelle's salt solution
customThe organic fraction was purified by SCX ion-exchange chromatography

Sources & evidence

ORD record: ord-c6664e8143744a36bb93f205570963f2
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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