Sodium borohydride → 6-(2-(Hydroxymethyl)-4-methoxyphenyl)-4-(methylthio)-2,3'-bipyridine-5-carbonitrile

HRID 81073Notes

Reaction equation

HRID 81073 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13]1[N:18]=[C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[C:15]([S:25][CH3:26])[C:14]=1[C:27]#[N:28])=[O:4]>CO.ClCCl>[OH:4][CH2:3][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13]1[N:18]=[C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[C:15]([S:25][CH3:26])[C:14]=1[C:27]#[N:28]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86665695HCID 86665695, compound

Product 1

HCID 669273036-(2-(Hydroxymethyl)-4-methoxyphenyl)-4-(methylthio)-2,3'-bipyridine-5-carbonitrileYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (2.2 mg, 0.058 mmol) was added to a solution of 6-(2-formyl-4-methoxyphenyl)-4-(methylthio)-2,3′-bipyridine-5-carbonitrile (4.3 mg, 0.012 mmol) in methanol (0.45 mL) and dichloromethane (0.450 mL) at room temperature. After 20 min at ambient temperature, the mixture was quenched with TEA (10 μL) and concentrated. Silica gel chromatography, eluting with 0-10% methanol in dichloromethane, gave 6-(2-(hydroxymethyl)-4-methoxyphenyl)-4-(methylthio)-2,3′-bipyridine-5-carbonitrile as white solid (2.8 mg, 65% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.12 (1H, δ, J=2.01 Hz), 8.72-8.77 (1H, m), 822-8.28 (1H, m), 7.60-7.65 (1H, m), 7.43-7.49 (2H, m), 7.11 (1H, δ, J=2.76 Hz), 6.97-7.02 (1H, m), 4.44 (2H, s), 3.90 (3H, s), 2.72 (3H, s); MS (ES+) 111/Z: 364 (M+H); LC retention time: 3.061 min (analytical HPLC Method A).

Workup

  1. customthe mixture was quenched with TEA (10 μL)
  2. concentrationconcentrated
  3. washSilica gel chromatography, eluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-306b589b96464f62aea71b37f76b685b
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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