Sodium borohydride → HCID 66649202, compound

HRID 2193783Notes

Reaction equation

HRID 2193783 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:18]=3)[S:13][C:6]=12.[BH4-].[Na+]>CCO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:29][C:27]1[CH:26]=[CH:25][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[N:15]=[CH:16][N:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:18]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:28]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58790027HCID 58790027, compound

Product 1

HCID 66649202HCID 66649202, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 702EthanolSolvent

Procedure

To a solution of thienopyridine 374 (0.25 g, 0.56 mmol) and nickel chloride hexahydrate (0.26 g, 1.1 mmol) in absolute EtOH (50 mL) was added sodium borohydride (0.085 g, 2.2 mmol) in small portions. The resulting mixture was stirred at r.t. for 1 h, then filtered through celite, run through a short plug of silica, eluting with 1:1 ethyl acetate/ethanol, and concentrated, affording title compound 375 (0.21 g, 91% yield). LRMS (M+H): 413.1.

Workup

  1. filtrationfiltered through celite
  2. washeluting with 1:1 ethyl acetate/ethanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3c5b9f95b4e344bd825bc51a665d105a
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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