Sodium borohydride → HCID 39150028, compound

HRID 2284619Notes

Reaction equation

HRID 2284619 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)[CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][OH:12])=[CH:9][N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 213456766-Bromoimidazo[1,2-a]pyridine-3-carbaldehyde

Product 1

HCID 39150028HCID 39150028, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stirring solution of 6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde [see Bioorg. Med. Chem. Let. 15(17), 5837-5844; 2007; Int'l Pat. App. Pub. no, 2011/055320] (1.5 g, 6.6 mmol) in MeOH (20 mL) was cooled to 0° C. and NaBH4 (0.50 g, 13.2 mmol) was added in portions for a period of 20 min. Cooling was removed after 1 h and allowed to stir for 3 h. The reaction mixture was quenched with water and concentrated by rotary evaporator to dryness. Subsequently, the solid concentrate was diluted with water and collected on the Buchner funnel by suction filtration. The solid was suction dried to obtain (6-bromoimidazo[1,2-a]pyridin-3-yl)methanol as a pale yellow crystalline solid (0.83 g). 1H NMR (300 MHz, DMSO-d6) δ 8.63 (dd, J=2.0, 0.9 Hz, 1H), 7.55 (dd, J=9.5, 0.9 Hz, 1H), 7.52 (s, 1H), 7.36 (dd, J=9.5, 2.0 Hz, 1H), 5.27 (t, J=5.4 Hz, 1H), 4.79 (d, J=5.3 Hz, 2H). See J. Med. Chem., 54(7), 2455-66 (2011).

Workup

  1. temperatureCooling
  2. customwas removed after 1 h
  3. customThe reaction mixture was quenched with water
  4. concentrationconcentrated by rotary evaporator to dryness
  5. concentrationSubsequently, the solid concentrate
  6. additionwas diluted with water
  7. filtrationcollected on the Buchner funnel by suction filtration
  8. customdried

Sources & evidence

ORD record
ord-fd4370cec8794e1c872966c9dcef5c7c
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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