Sodium borohydride → HCID 22339372, compound

HRID 585139Notes

Reaction equation

HRID 585139 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:26]2[C:31](=[O:32])[NH:30][C:29](=[O:33])[CH:28]=[N:27]2)[CH:5]=[C:6]([CH3:25])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:10]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:26]2[C:31](=[O:32])[NH:30][C:29](=[O:33])[CH:28]=[N:27]2)[CH:5]=[C:6]([CH3:25])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[OH:24])[CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22339619HCID 22339619, compound

Product 1

HCID 22339372HCID 22339372, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 2-{3-chloro-4-[3-(4-fluoro-benzoyl)-4-hydroxy-phenoxy]-5-methyl-phenyl}-2H-[1,2,4]triazine-3,5-dione (0.4 g) in methanol (10 mL) was added sodium borohydride (32 mg). After 30 min, the reaction solution was concentrated in vacuo, partitioned between 1N hydrochloric acid and ethyl acetate, the organic phase dried (Na2SO4), concentrated in vacuo and flash chromatographed on silica gel (5% ethanol/dichloromethane) to afford the title compound of Step C as a colorless foam, 72 mg. MS Calc.:469.8; Found:467.9.

Workup

  1. concentrationthe reaction solution was concentrated in vacuo
  2. custompartitioned between 1N hydrochloric acid and ethyl acetate
  3. dry with materialthe organic phase dried (Na2SO4)
  4. concentrationconcentrated in vacuo and flash
  5. customchromatographed on silica gel (5% ethanol/dichloromethane)

Sources & evidence

ORD record
ord-21baca2cdefd457f9bfd3a0e092b4a09
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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