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

HRID 2382718Notes

Reaction equation

HRID 2382718 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), w-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-8621fee23c924935a00563390f0b4431
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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