Water → 5H,6H,7H,8H-imidazo[1,2-a]pyridin-6-ol

HRID 1055172Notes

Reaction equation

HRID 1055172 reaction equation
B(Br)(Br)Br.C[O:6][CH:7]1[CH2:12][N:11]2[CH:13]=[CH:14][N:15]=[C:10]2[CH2:9][CH2:8]1.O>ClCCl>[N:15]1[CH:14]=[CH:13][N:11]2[CH2:12][CH:7]([OH:6])[CH2:8][CH2:9][C:10]=12

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 252095116-Methoxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Product 1

HCID 252091725H,6H,7H,8H-imidazo[1,2-a]pyridin-6-olYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add boron tribromide (1.24 mL; 2.0 equiv; 13.14 mmoles) to a solution of 6-methoxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1.0 g; 1.0 equiv; 6.57 mmoles) in dichloromethane (40 mL) dropwise and stir at ambient temperature for 4 hours. Add water (10 mL) and stir for 20 minutes, then concentrate the mixture. Add methanol (20 mL) and load the solution onto an scx ion-exchange column. Purify the product by eluting with methanol followed by 2M ammonia in methanol to give 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol (0.908 g; 80% yield), which crystallizes upon standing. MS (m/z): 139 (M+1).

Workup

  1. concentrationconcentrate the mixture
  2. customPurify the product
  3. washby eluting with methanol

Sources & evidence

ORD record
ord-fddcd78e3e6248ecba5c5ba926df5aa3
Source dataset
uspto-grants-2016_07
Patent number
US09394317B2

Reaction notes

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