Sodium borohydride → HCID 22339372, compound

HRID 1006216Notes

Reaction equation

HRID 1006216 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-68b3cde8893e4d5db4371420249f874b
Source dataset
uspto-grants-2004_09
Patent number
US06787652B1

Reaction notes

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