Sodium borohydride → 3'-(7-Hydroxymethylimidazo[1,2-alpha]-pyridin3-yl)biphenyl-2-carbonitrile

HRID 985545Notes

Reaction equation

HRID 985545 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1)=[O:2].[BH4-].[Na+]>C(Cl)(Cl)Cl.CO>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 98583783'-(7-Formylimidazo[1,2-alpha]pyridin-3-yl)biphenyl-2-carbonitrile

Product 1

HCID 98803563'-(7-Hydroxymethylimidazo[1,2-alpha]-pyridin3-yl)biphenyl-2-carbonitrileYield 75.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

3′-(7-Formylimidazo[1,2-α]pyridin-3-yl)biphenyl-2-carbonitrile (140 mg, 0.43 mmol) was suspended in chloroform (4 ml) and methanol (7 ml), sodium borohydride (82 mg, 2.17 mmol) added portionwise over 5 min then the reaction was heated under reflux for 1.5 h. The mixture was evaporated to dryness, the residue diluted with water (40 ml) and extracted with chloroform (2×50 ml). The combined organics were washed with brine (40 ml), dried over anhydrous sodium sulfate and evaporated to dryness. Purification was effected by silica gel chromatography eluting with dichloromethane and 1% conc. ammonia on a gradient of methanol (1-5%). The solid obtained was triturated with diethyl ether which gave the title compound (106 mg, 75%) as a white powder. 1H NMR (400 MHz, MeOD) δH 4.70 (2H, d, J 1), 6.97 (1H, dd, J 7 and 2), 7.55-7.60 (2H, m), 7.61-7.65 (1H, m), 7.67-7.80 (5H, m), 7.84-7.88 (2H, m), 8.65 (1H, dd, J 7 and 1); m/z (ES+) 326 (M++H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 1.5 h
  3. customThe mixture was evaporated to dryness
  4. additionthe residue diluted with water (40 ml)
  5. extractionextracted with chloroform (2×50 ml)
  6. washThe combined organics were washed with brine (40 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness
  9. customPurification
  10. washeluting with dichloromethane and 1% conc. ammonia on a gradient of methanol (1-5%)
  11. customThe solid obtained
  12. customwas triturated with diethyl ether which

Sources & evidence

ORD record
ord-24199e1bde60479b8b7f22ff90089692
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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