Sodium borohydride → (R)-N-((5-Bromo-4-chloropyridin-3-yl)methyl)-2-methylpropane-2-sulfinamide

HRID 1774781Notes

Reaction equation

HRID 1774781 reaction equation
[Br:1][C:2]1[C:3]([Cl:16])=[C:4](/[CH:8]=[N:9]/[S@@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[CH:5]=[N:6][CH:7]=1.CC([S@](N)=O)(C)C.BrC1C(Cl)=C(C=O)C=NC=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([Cl:16])=[C:4]([CH2:8][NH:9][S@@:10]([C:12]([CH3:14])([CH3:13])[CH3:15])=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 717423075-Bromo-4-chloropyridine-3-carbaldehydeHCID 178455564HCID 178455564, compound

Product 1

HCID 86679149(R)-N-((5-Bromo-4-chloropyridin-3-yl)methyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-2-Methyl-propane-2-sulfinic acid 1-(5-bromo-4-chloro-pyridin-3-yl)-meth-(E)-ylideneamide, prepared from (R)-2-methylpropane-2-sulfinamide and 5-bromo-4-chloro-pyridine-3-carbaldehyde in analogy to procedure described for the preparation of intermediate A-35 [A], has been reduced with NaBH4 in MeOH in analogy to the procedure described for the preparation of intermediate A-35 [B] to give the title compound as a yellow oil. MS: 325.2 (M+H+).

Workup

  1. customdescribed for the preparation of intermediate
  2. customdescribed for the preparation of intermediate A-35 [B]

Sources & evidence

ORD record
ord-1bbcf602265c4e18bb6aaf76c543ad8c
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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