Water → HCID 86728280, compound

HRID 1776895Notes

Reaction equation

HRID 1776895 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]3[C:17]=2[CH:18]=[O:19])[C:5]([Cl:8])=[N:6][CH:7]=1.[BH4-].[Na+].O>CO>[Br:1][C:2]1[CH:3]=[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])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86728279HCID 86728279, compound

Product 1

HCID 86728280HCID 86728280, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(5-bromo-2-chloropyridin-3-yl)imidazo[1,2-a]pyridine-3-carbaldehyde (100 mg, 0.29 mmol) in MeOH (5 mL), NaBH4 (20 mg, 0.53 mmol) was added at 0° C. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was added water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using PTLC (eluted with dichloromethane:MeOH=30:1) to provide (2-(5-bromo-2-chloropyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)methanol (30 mg, yield: 29%). 1H-NMR (DMSO, 400 MHz) δ 8.66 (d, J=2.4 Hz, 1H), 8.49 (d, J=6.8 Hz, 1H), 8.25 (d, J=2.4 Hz, 1H), 7.64 (d, J=9.2 Hz, 1H), 7.35˜7.40 (m, 1H), 7.03˜7.07 (m, 1H), 5.33 (t, J=5.2 Hz, 1H), 4.75 (d, J=5.2 Hz, 2H). MS (M+H)+: 338/340.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified
  6. washPTLC (eluted with dichloromethane:MeOH=30:1)

Sources & evidence

ORD record
ord-e9200169fa0248a2abd66b9db4a356f7
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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