Water → HCID 71295597, compound

HRID 1776888Notes

Reaction equation

HRID 1776888 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](O)=[C:4]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]3[C:17]=2[CH2:18][OH:19])[CH:3]=1.O>C1(C)C=C(C)C=C(C)C=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]3[N:10]=[C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]4[C:17]=3[CH2:18][O:19][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 71295574HCID 71295574, compound

Product 1

HCID 71295597HCID 71295597, compoundYield 553.5%

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Conditions

Temperature
170 °C

Procedure

4-bromo-2-(3-(hydroxymethyl)imidazo[1,2-a]pyridin-2-yl)phenol (0.2 g, 0.06 mmol) was dissolved in mesitylene (1 mL). The mixture was stirred at 170° C. for 6 hours, and then cooled to 25° C. H2O (20 mL) was added and extracted with EtOAc (3*50 mL), washed by brine (50 mL). After concentrated, the resulting residue was purified using Prep-TLC (petroleum ether:EtOAc=1:1) to provide 2-bromo-6H-chromeno[4′,3′:4,5]imidazo[1,2-a]pyridine (100 mg, yield: 53.0%). 1H-NMR (CDCl3, 400 MHz) δ 7.98˜7.99 (m, 1H), 7.74˜7.76 (m, 1H), 7.66˜7.68 (m, 1H), 7.21˜7.28 (m, 2H), 6.82˜6.90 (m, 2H), 5.70 (s, 2H). MS (M+H)+: 301/303.

Workup

  1. temperaturecooled to 25° C
  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-857f1a79ae334645ab09775581be8293
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

Loading…