Water → HCID 86728277, compound

HRID 1776886Notes

Reaction equation

HRID 1776886 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19]C)=[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.B(Br)(Br)Br.O>ClCCl>[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

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86728276HCID 86728276, compound

Product 1

HCID 86728277HCID 86728277, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

2-(5-bromo-2-methoxyphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde (0.1 g, 3 mmol) was dissolved in dichloromethane (0.5 mL) at −78° C. BBr3 (1 mL) was added by dropwise stirred for 2 hours at that temperature. Then warmed to 25° C. and stirred for 10 hours. H2O (20 mL) was added by dropwise at −78° C. and extracted with EtOAc (3*50 mL), washed by aq NaHCO3 (3*50 mL) and brine (50 mL). After concentrated, the resulting residue was purified using Prep-TLC (petroleum ether:EtOAc=3:1) to provide 2-(5-bromo-2-hydroxyphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde (40 mg, yield: 48%). 1H-NMR (CDCl3, 400 MHz) δ 10.29 (s, 1H), 9.76 (s, 1H), 7.78˜7.79 (m, 2H), 7.65˜7.69 (m, 1H), 7.46˜7.48 (m, 1H), 7.20˜7.22 (m, 1H), 7.00˜7.02 (m, 1H). MS (M+H)+: 317/319.

Workup

  1. stirringstirred for 10 hours
  2. extractionextracted with EtOAc (3*50 mL)
  3. washwashed by aq NaHCO3 (3*50 mL) and brine (50 mL)
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-0bc6fab644f24d7d8d7d4098a7f16542
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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