Sodium borohydride → HCID 71002779, compound

HRID 1626997Notes

Reaction equation

HRID 1626997 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:16]1[CH:17]=[CH:18][C:19]([CH2:23][OH:24])=[N+:20]([CH3:22])[CH:21]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:16]1[CH2:17][CH2:18][CH:19]([CH2:23][OH:24])[N:20]([CH3:22])[CH:21]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70978409HCID 70978409, compound

Product 1

HCID 71002779HCID 71002779, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]-2-(hydroxymethyl)-1-methylpyridinium (36 mg, 0.092 mmol) in methanol (1 ml) was added sodium borohydride (28.0 mg, 0.74 mmol) in 4 portions over 4 hours. After stirring for 16 hours, the mixture was purified via silica gel chromatography (methanol/dichloromethane gradient), providing the titled compound: 1H NMR (500 MHz, d6-DMSO) δ 7.91 (1H, d, J=8.50 Hz), 7.40 (1H, d, J=8.46 Hz), 5.76 (1H, s), 4.56 (1H, m), 4.52 (2H, s), 3.67-3.61 (1H, m), 3.55-3.49 (1H, m), 2.64 (1H, s), 2.42 (3H, s), 2.30-2.19 (2H, m), 1.24 (1H, s), 0.96 (9H, s) ppm. LRMS m/z (M+H) 393.0 and 395.0 found, 393.1 and 395.1 required.

Workup

  1. customthe mixture was purified via silica gel chromatography (methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-02cbf8c1181a4becaea0acf0292da080
Source dataset
uspto-grants-2014_07
Patent number
US08785482B2

Reaction notes

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