Ammonium Acetate → 1-[3-(3,5-Difluorophenyl)-5-methylimidazo[1,2-a]pyridin-2-yl]ethanamine

HRID 1478683Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[C:14]([CH3:18])=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[C:19](=O)[CH3:20])[CH:5]=[C:6]([F:8])[CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[C:14]([CH3:18])=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH:19]([NH2:28])[CH3:20])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 1-[3-(3,5-difluorophenyl)-5-methylimidazo[1,2-a]pyridin-2-yl]ethanone (0.23 g, 0.82 mmol) in methanol (9.5 mL) was treated with ammonium acetate (0.63 g, 8.2 mmol) and heated at 65° C. for 1 h. The reaction mixture was treated with sodium cyanoborohydride (0.15 g, 2.5 mmol) and heated at 65° C. for 4 h. The reaction mixture was concentrated and purified by preparative LCMS to give the desired product (0.13 g, 56%) as a colorless oil. LCMS for C16H16F2N3 (M+H)+: m/z=288.1.

Workup

temperatureheated at 65° C. for 4 h
concentrationThe reaction mixture was concentrated
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-b1af0865ec414d95a012f218ce0c3bbc
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403847B2

Reaction notes

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