Sodium borohydride → [6-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)pyridazin-3-yl]methanol

HRID 1644875Notes

Reaction equation

HRID 1644875 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:33]=[N:32][C:31]([C:34](OC)=[O:35])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][N:9]=1)[CH:5]([CH3:7])[CH3:6]>CCO>[CH3:3][C:4]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:33]=[N:32][C:31]([CH2:34][OH:35])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][N:9]=1)[CH:5]([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57910811Methyl 6-(4-{1,2-dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)pyridazine-3-carboxylate

Product 1

HCID 24758848[6-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)pyridazin-3-yl]methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (14.0 mg, 0.362 mmol) was added to a stirred solution of 5c (113 mg, 0.241 mmol) in EtOH (2.00 mL) at 0° C., and the resulting mixture was allowed to warm to rt. After approximately 12 h, the reaction mixture was cooled to 0° C. and quenched by the addition of aqueous 1N HCl. The resulting mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 30%-100% EtOAc/hexanes as eluent) afforded the title compound 5d. m/z (ES) 441 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.61 (d, 1H, J=3.2 Hz), 8.40 (m, 1H), 7.97 (d, 2H, J=8.2 Hz), 7.83 (d, 1H, J=8.7 Hz), 7.75 (m, 1H), 7.52 (m, 4H), 7.26 (m, 1H), 7.19 (m, 2H), 5.23 (s, 2H), 3.09 (m, 1H, J=6.6 Hz), 1.72 (s, 3H), 0.88 (d, 3H, J=6.6 Hz), 0.83 (d, 3H, J=6.6 Hz).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customquenched by the addition of aqueous 1N HCl
  3. additionThe resulting mixture was poured into saturated aqueous sodium bicarbonate
  4. extractionextracted three times with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 30%-100% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-bd0b79b8ec68451b862b86f1149c1550
Source dataset
uspto-grants-2012_02
Patent number
US08124628B2

Reaction notes

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