Diethyl Ether → tert-Butyl 2-(3-bromophenyl)-5-chloro-7,8-dimethylimidazo[1,2-a]pyridine-6-carboxylate

HRID 1482062Notes

Reaction equation

HRID 1482062 reaction equation
[NH2:1][C:2]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([Cl:17])[N:3]=1.[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25](OC)(OC)[CH2:26]Br)[CH:20]=1.CCOCC>ClC1C=CC=CC=1>[Br:18][C:19]1[CH:20]=[C:21]([C:25]2[N:1]=[C:2]3[C:14]([CH3:15])=[C:13]([CH3:16])[C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7])=[C:4]([Cl:17])[N:3]3[CH:26]=2)[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 1183088131-Bromo-3-(2-bromo-1,1-dimethoxyethyl)benzeneHCID 118308920tert-Butyl 6-amino-2-chloro-4,5-dimethylnicotinate

Product 1

HCID 118308922tert-Butyl 2-(3-bromophenyl)-5-chloro-7,8-dimethylimidazo[1,2-a]pyridine-6-carboxylateYield 90.8%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A slurry of tert-butyl 6-amino-2-chloro-4,5-dimethylnicotinate (1.2 g, 4.7 mmol, 1 equiv) and 1-bromo-3-(2-bromo-1,1-dimethoxyethyl)benzene (2.3 g, 7.0 mmol, 1.5 equiv) in chlorobenzene (23 mL) was heated at reflux for 1.5 h. Upon cooling to ambient temperature, the reaction was added slowly to ether. The slurry was stirred for 15 min and the filtered to provide the product as a HBr salt (1.86 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ 8.73 (s, 1H), 8.32 (s, 1H), 8.12 (d, J=7.8 Hz, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.47-7.40 (m, 1H), 2.56 (s, 3H), 2.30 (s, 3H), 1.60 (s, 9H); LCMS (ESI, M+1): 435.05.

Workup

  1. temperatureat reflux for 1.5 h
  2. filtrationthe filtered

Sources & evidence

ORD record
ord-6798ce449a2b407ba3b83f1d2beb6b6a
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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