Borohydride → 2-Methylpentane

HRID 751702Notes

Reaction equation

HRID 751702 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:23])[CH2:9][NH:10][C:11]([C:13]2[NH:22][C:16]3=[CH:17][N:18]=[C:19]([Cl:21])[CH:20]=[C:15]3[CH:14]=2)=[O:12])=[CH:4][CH:3]=1.[BH4-]>C(O)C>[CH3:2][CH2:3][CH2:4][CH:5]([CH3:8])[CH3:6].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:23])[CH2:9][NH:10][C:11]([C:13]2[NH:22][C:16]3=[CH:17][N:18]=[C:19]([Cl:21])[CH:20]=[C:15]3[CH:14]=2)=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 28123BorohydrideHCID 59753577HCID 59753577, compound

Product 2

HCID 78922-MethylpentaneHCID 11348194HCID 11348194, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(4-fluorophenyl)-2-oxoethyl]amide EXAMPLE 48 (0.05 g, 151 mmol) in ethanol (5 mL, absolute) was added polymer-supported borohydride (2.5 mmol/g, 0.09 g, 226 mmol) and the mixture sonicated with gentle warming until the ketone had dissolved. The reaction mixture was stirred for 2 days at rt then filtered, washing with methanol. The filtrate was evaporated to dryness in vacuo to give a colourless oil. Purification via flash column chromatography (SiO2, ethyl acetate:isohexane, 1:1, v/v) gave the title compound as a white solid. m/z (ES+)=334 [M+H]+; RT=2.93 min.

Workup

  1. customthe mixture sonicated
  2. dissolutionhad dissolved
  3. filtrationthen filtered
  4. washwashing with methanol
  5. customThe filtrate was evaporated to dryness in vacuo
  6. customto give a colourless oil
  7. customPurification via flash column chromatography (SiO2, ethyl acetate

Sources & evidence

ORD record
ord-a4460e1ca34c4c5c8911f28c9750a4aa
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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