Sodium cyanoborohydride → HCID 58975187, compound

HRID 737065Notes

Reaction equation

HRID 737065 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([CH3:27])=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[BH3-]C#N.[Na+]>C(O)(C(F)(F)F)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:10]=[CH:11][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]([CH3:27])[CH2:19]3)(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 58975171HCID 58975171, compound

Product 1

HCID 58975187HCID 58975187, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
2.5 °C

Procedure

Add N-(4-Fluoro-benzyl)-4-(3-methyl-indole-1-sulfonyl)-benzamide (0.106 g, 0.25 mmol) portionwise to a stirring mixture of NaCNBH3 (0.074 g, 1.2 mmol, in TFA (5.0 mL) at 0 to 5° C. under N2. Stir the mixture for 15 minutes at 0-5° C., allow to warm to ambient temperature and stir for 1 h. add NaCNBH3 (0.074 g, 1.2 mmol) and stir the reaction is for 2 h dilute with H2O (13.0 mL) and work up as described in the above example. Chromatograph and elute with EtOAc-hexane (0-50%) to give 0.075 g of the title compound: Mass spectrum (m/e) (M+H) 425.1335; found 425.1341.

Workup

  1. customat 0 to 5° C.
  2. temperatureto warm to ambient temperature
  3. stirringstir for 1 h.
  4. stirringstir the reaction
  5. waitis for 2 h
  6. washChromatograph and elute with EtOAc-hexane (0-50%)

Sources & evidence

ORD record
ord-6bf021364e5044eab038d9a0e2af2d49
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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