Water → HCID 71295574, compound

HRID 1776887Notes

Reaction equation

HRID 1776887 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:19])=[C:6]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH:17]=[O:18])[CH:7]=1.[BH4-].[Na+].O>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:19])=[C:6]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][OH:18])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86728277HCID 86728277, compound

Product 1

HCID 71295574HCID 71295574, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

2-(5-bromo-2-hydroxyphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde (0.19 g, 0.63 mmol) was dissolved in MeOH (2 mL) at 0° C. NaBH4 (0.072 g, 1.9 mmol) was added portionwise. After addition, the mixture was stirred at 25° C. for 30 minutes, and then H2O (20 mL) was added by dropwise. Extracted with EtOAc (3*50 mL), washed by brine (50 mL). After concentrated, the resulting residue was purified using Prep-TLC (petroleum ether:EtOAc=3:1) to provide 4-bromo-2-(3-(hydroxymethyl)imidazo[1,2-a]pyridin-2-yl)phenol (150 mg, yield: 85%). 1H-NMR (CDCl3, 400 MHz) δ 8.33˜8.35 (m, 1H), 7.72 (s, 1H), 7.62˜7.64 (m, 1H), 7.31˜7.37 (m, 2H), 6.92˜7.01 (m, 2H), 5.20 (s, 2H). MS (M+H)+: 319/321.

Workup

  1. additionAfter addition
  2. extractionExtracted with EtOAc (3*50 mL)
  3. washwashed by brine (50 mL)
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-63ca7e3c28624b758cd821e460a6d2a1
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

Loading…