Sodium borohydride → HCID 68681649, compound

HRID 1594348Notes

Reaction equation

HRID 1594348 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH:21]=[CH:20][C:19]([CH:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[OH:23])=[CH:18][CH2:17]2)=[CH:11][CH:10]=1.[BH4-].[Na+]>C(O)C.O>[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][C:19]([CH:22]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:28][CH:29]=3)[OH:23])=[CH:18][CH2:17]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 131726694HCID 131726694, compound

Product 1

HCID 68681649HCID 68681649, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 1.0 gram (0.0021 mole) of {1-[(4-pyrimidin-2-yloxyphenyl)methyl](4-pyridyl)}[4-(trifluoromethyl)phenyl]methanol, hydrochloride salt in 30 mL of ethanol was cooled in an ice-water bath, and 0.1 gram (0.0026 mole) of sodium borohydride was added in one portion. Upon completion of addition, the reaction mixture was stirred at about 10° C. to 20° C. during a three-hour period. After this time the reaction mixture was diluted with 100 mL of water and extracted with two 75 mL portions of ethyl acetate. The combined extracts were washed with one 75 mL portion of aqueous 10% lithium chloride, and the combination was dried with sodium sulfate. The mixture was then filtered and the filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on neutral alumina (6% water) using 1% to 2% methanol/methylene chloride mixtures as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.44 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. extractionextracted with two 75 mL portions of ethyl acetate
  3. washThe combined extracts were washed with one 75 mL portion of aqueous 10% lithium chloride
  4. dry with materialthe combination was dried with sodium sulfate
  5. filtrationThe mixture was then filtered
  6. concentrationthe filtrate was concentrated under reduced pressure to a residue
  7. customThe residue was purified with column chromatography on neutral alumina (6% water)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd6bb842c56745eba48b7e5ddc317f10
Source dataset
uspto-grants-2007_11
Patent number
US07300946B2

Reaction notes

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