Sodium borohydride → HCID 15950718, compound

HRID 1619209Notes

Reaction equation

HRID 1619209 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH2:10][CH2:11][N:12]([C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:13][CH:14]=2)=[O:8])=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]=[CH:3][C:4]([CH:7]([C:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:16]=[CH:17][CH:18]=[CH:19][N:20]=3)[CH2:11][CH:10]=2)[OH:8])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 15950716HCID 15950716, compound

Product 1

HCID 15950718HCID 15950718, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of biphenyl-4-yl-(1-pyrimidin-2-yl-1,2,3,6-tetrahydro-pyridin-4-yl)-methanone (12.2 mg, 0.0355 mmol) in methanol (0.5 ml), was added CeCl3 heptahydate (13.2 mg, 0.0355 mmol) and sodium borohydride (1.5 mg, 0.0355 mmol) at room temperature. The mixture was stirred for 1 hour and diluted with EtOAc (10 ml). The mixture was washed with water (5 ml), brine (5 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (6% MeOH/CH2Cl2) to give the title compound (12 mg, 98%) as a white gel: 1H NMR (CDCl3, 400 MHz) δ 8.36 (d, J=6.4 Hz, 2H), 7.62-7.37 (m, 9H), 6.46 (t, J=6.4 Hz, 1H), 6.02 (m, 1H), 5.24 (m, 1H), 4.31 (m, 2H), 3.96 (m, 1H), 3.83 (m, 1H), 2.14 (m, 2H); MS calc'd for C22H22N3O [M+H]+: 344; Found: 344.

Workup

  1. washThe mixture was washed with water (5 ml), brine (5 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto furnish the crude product
  6. customThis material was purified by column chromatography (6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ca12bef6d1b14dc5a9030e8367397359
Source dataset
uspto-grants-2014_07
Patent number
US08772291B2

Reaction notes

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