Sodium borohydride → HCID 178428427, compound

HRID 218487Notes

Reaction equation

HRID 218487 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]3[C:17]([C:18]#[N:19])=[C:16]([CH3:20])[NH:15][C:14]([CH3:21])=[C:13]3[C:22]#[N:23])[CH:10]=2)[NH:5][N:4]=1)=[O:2].[BH4-].[Na+]>CO.[Cl-].[Na+].O>[OH:2][CH2:1][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]3[C:13]([C:22]#[N:23])=[C:14]([CH3:21])[NH:15][C:16]([CH3:20])=[C:17]3[C:18]#[N:19])[CH:10]=2)[NH:5][N:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178428426HCID 178428426, compound

Product 1

HCID 178428427HCID 178428427, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 4-(3-formyl-1H-indazol-5-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (200 mg, 0.66 mmol) in MeOH was added NaBH4 (50 mg) at rt. After 1 hr, the reaction was diluted with brine, extracted with EtOAc, washed with water, and dried. Concentration followed by purification through flash chromatography afforded 1,4-dihydro-4-[3-(hydroxymethyl)-1H-indazol-5-yl]-2,6-dimethyl-3,5-pyridinedicarbonitrile (100 mg, 50%) as a yellow solid (Cpd. No. 144, Table 2). 1H-NMR (400 MHz, DMSO-D6): δ=9.55 (s, 1H), 7.68 (s, 1H), 7.52 (d, 1H), 7.26 (d, 1H), 5.24 (t, 1H), 4.78 (d, 2H), 4.55 (s, 1H), 2.03 (s, 6H) ppm.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water
  3. customdried
  4. concentrationConcentration
  5. customfollowed by purification through flash chromatography

Sources & evidence

ORD record
ord-1a1d2852471e4f64bd9b07db7f8e7f69
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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