Sodium borohydride → HCID 66649202, compound

HRID 418727Notes

Reaction equation

HRID 418727 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-ee02b6adf1ad417a806794b30137d351
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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