Sodium borohydride → HCID 66701642, compound

HRID 1186771Notes

Reaction equation

HRID 1186771 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:17]1[N:18]([CH3:34])[C:19](=[O:33])[CH:20]=[CH:21][C:22]=1[NH:23][S:24]([C:27]1([CH2:30][CH:31]=[O:32])[CH2:29][CH2:28]1)(=[O:26])=[O:25])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:17]1[N:18]([CH3:34])[C:19](=[O:33])[CH:20]=[CH:21][C:22]=1[NH:23][S:24]([C:27]1([CH2:30][CH2:31][OH:32])[CH2:29][CH2:28]1)(=[O:26])=[O:25])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86664507HCID 86664507, compound

Product 1

HCID 66701642HCID 66701642, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the crude tert-butyl (2-fluoro-4-iodophenyl)[1-methyl-6-oxo-3-({[1-(2-oxoethyl)cyclopropyl]sulfonyl}amino)-1,6-dihydropyridin-2-yl]carbamate (88% UV, 97 mg, 0.160 mmol) in MeOH at 0° C. under a nitrogen atmosphere was added NaBH4 (4 eq, 25 mg, 0.641 mmol). The reaction mixture was stirred at this temperature for 1 hour and then allowed to warm up to room temperature. The solvent was removed under reduced pressure, the residue partitioned between EtOAc (10 ml), H2O (5 ml) and 1N aq HCl (5 ml). The aqueous phase was separated and extracted twice with EtOAc (10 ml). The combined organic layers were washed with brine (20 ml), dried (silicone filter) and concentrated under reduced pressure. The crude material was purified by flash chromatography (Biotage system) to afford the title compound (77 mg, 79%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between EtOAc (10 ml), H2O (5 ml) and 1N aq HCl (5 ml)
  3. customThe aqueous phase was separated
  4. extractionextracted twice with EtOAc (10 ml)
  5. washThe combined organic layers were washed with brine (20 ml)
  6. customdried
  7. filtration(silicone filter)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by flash chromatography (Biotage system)

Sources & evidence

ORD record
ord-31614f3e1ee1488c8a60d3fee0ba6820
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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