Methanol → Methyl 2-phenylimidazo[1,2-a]pyridine-7-carboxylate

HRID 908203Notes

Reaction equation

HRID 908203 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH2:10])[CH:5]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O.C([O-])(O)=O.[Na+].CO>O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][N:7]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:10]=[C:6]2[CH:5]=1)=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 6259Phenacyl bromideHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 352572Methyl 2-phenylimidazo[1,2-a]pyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-isonicotinic acid methyl ester (5 g, 32 mmol), ω-bromoacetophenone (6.47 g, 32 mmol), NaHCO3 (2.95 g, 35 mmol) and methanol (30 ml) was heated under an atmosphere of argon to reflux (3 h). After cooling, water (20 ml) was added, the mixture was stirred at r.t. (15 min), and filtered. The obtained solid was washed (water, methanol, diethyl ether) and dried under vacuum. The product (6.8 g, 85%) was used in the next step without further purification. MS (m/e)=253.2 [M+H+].

Workup

  1. temperaturewas heated under an atmosphere of argon
  2. temperatureto reflux (3 h)
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. washThe obtained solid was washed (water, methanol, diethyl ether)
  6. customdried under vacuum
  7. customThe product (6.8 g, 85%) was used in the next step without further purification

Sources & evidence

ORD record
ord-ae0f4d88f6644fb087b81ff743fd291f
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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