Sodium borohydride → HCID 58790376, compound

HRID 2193803Notes

Reaction equation

HRID 2193803 reaction equation
[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][N:5]1[CH:10]=[C:9]([C:11]2[S:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:22]=3[F:30])[CH:12]=2)[CH:8]=[CH:7][C:6]1=[O:31].[BH4-].[Na+]>CO.C1COCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:17]2[CH:16]=[CH:15][N:14]=[C:13]3[CH:12]=[C:11]([C:9]4[CH:8]=[CH:7][C:6](=[O:31])[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:32])[CH:10]=4)[S:19][C:18]=23)=[C:22]([F:30])[CH:23]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydride2×HCID 58790424HCID 58790424, compound

Product 1

HCID 58790376HCID 58790376, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalyst2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the nitro compound 421 (0.103 g, 0.227 mmol) in methanol (2 mL) and THF (2 ml) at 0° C. was added nickel chloride hexahydrate (0.162 g, 0.681 mmol) followed by sodium borohydride (28 mg, 0.749 mmol). After one hour of stirring at 0° C. another portion of nickel chloride hexahydrate (0.108 g, 0.458 mmol) and sodium borohydride (19 mg, 0.50 mmol) were added. The reaction mixture was then stirred at room temperature for 5 hours before it was concentrated and treated with 1N HCl(aq) and dichloromethane. The mixture was stirred for 10 minutes and then basified to pH 10 by the addition of NH4OH. The basified solution was then extracted with dichloromethane. The extract was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (eluent a gradient of 10 to 100% methanol in ethyl acetate) to give the title compound 422 as yellow solid (26 mg, 27% yield). MS (m/z): 425.0 (M+H).

Workup

  1. additionwere added
  2. concentrationwas concentrated
  3. additiontreated with 1N HCl(aq) and dichloromethane
  4. stirringThe mixture was stirred for 10 minutes
  5. additionbasified to pH 10 by the addition of NH4OH
  6. extractionThe basified solution was then extracted with dichloromethane
  7. dry with materialThe extract was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography (eluent a gradient of 10 to 100% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-d424670de320414ca7051d69f5fcc2ed
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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