Sodium borohydride → HCID 86626983, compound

HRID 729993Notes

Reaction equation

HRID 729993 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][C:12]([C:14]2[N:19]=[C:18]([NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[C:17]([N+:27]([O-])=O)=[CH:16][CH:15]=2)=[C:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:10]=1.[BH4-].[Na+]>CO.[Pd]>[NH2:27][C:17]1[C:18]([NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[N:19][C:14]([C:12]2[NH:13][C:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])=[N:10][C:11]=2[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86626984HCID 86626984, compound

Product 1

HCID 86626983HCID 86626983, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add 10% Pd/C (0.033 g) to a stirring solution of propane-2-sulfonic acid {6-[2-(2,6-difluorophenyl)-5-phenyl-3H-imidazol-4-yl]-3-nitropyridin-2-yl}amide (0.33 g, 0.66 mmol) in MeOH (10 mL). Add sodium borohydride (0.124 g, 3.3 mmol) in portions and with stirring under nitrogen for 15 min. Filter the catalyst and concentrate. Dilute with EtOAc (20 mL) and extract successively with saturated NaHCO3 and saturated aqueous NaCl. Dry the organic layer over Na2SO4 and concentrate to give the title compound (0.3 g, 98%).

Workup

  1. filtrationFilter the catalyst
  2. concentrationconcentrate
  3. additionDilute with EtOAc (20 mL)
  4. extractionextract successively with saturated NaHCO3 and saturated aqueous NaCl
  5. dry with materialDry the organic layer over Na2SO4
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-54f8310fa37c4db99d9c50091a1253c1
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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