Imidazo[1,2-a]pyridin-8-ylmethanol → HCID 178488119, compound

HRID 1789197Notes

Reaction equation

HRID 1789197 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.O[CH2:14][C:15]1[C:16]2[N:17]([CH:21]=[CH:22][N:23]=2)[CH:18]=[CH:19][CH:20]=1>Br.C(O)(=O)C>[N:23]1[CH:22]=[CH:21][N:17]2[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][S:1][C:2]3[NH:6][C:5]4[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:4]=4[N:3]=3)[C:16]=12

Participants

5

Reactant 2

HCID 11029987Imidazo[1,2-a]pyridin-8-ylmethanolHCID 178488032HCID 178488032, compound

Product 1

HCID 178488119HCID 178488119, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A mixture of 2.92 g (23 mmole) of 3-hydroxymethyl-2-pyridinamine, 6.15 g (35 mmole) of chloroacetaldehyde, and 2.0 g (35 mmole) of sodium bicarbonate in 100 ml of ethanol was heated at reflux for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to a solid. Recrystallization from diethyl ether yielded 4.4 g of 8-hydroxymethylimidazo[1,2-a]pyridine, as confirmed by the nmr and infrared spectra. A mixture of 683 mg (3.8 mmole) of 2-mercapto-5-methoxybenzimidazole and 700 mg (3.8 mmole) of 8-hydroxymethylimidazo[1,2-a]pyridine was dissolved in 3 ml of 30% hydrogen bromide in acetic acid and heated on a steam bath. After being cooled to room temperature, the mixture was partitioned between 5% aqueous sodium hydroxide and dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated to yield the title compound as an oil. Structure assignment was supported by the nmr and infrared spectra.

Workup

  1. temperatureheated on a steam bath
  2. customthe mixture was partitioned between 5% aqueous sodium hydroxide and dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa237b32af6b4b098a33a40beb816430
Source dataset
uspto-grants-1987_08
Patent number
US04687775

Reaction notes

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