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Sodium borohydride → (R)-2-Methyl-propane-2-sulfinic acid (5-bromo-4-methyl-pyridin-3-ylmethyl)-amide

HRID 1774782
Notes
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Reaction equation

HRID 1774782 reaction equation
[Br:1][C:2]1[C:3]([CH3:16])=[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(C)=C(C=O)C=NC=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([CH3:16])=[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 222383375-Bromo-4-methylpyridine-3-carbaldehydeHCID 178421701HCID 178421701, compound

Product 1

HCID 86679150(R)-2-Methyl-propane-2-sulfinic acid (5-bromo-4-methyl-pyridin-3-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

(R)-2-Methyl-propane-2-sulfinic acid 1-(5-bromo-4-methyl-pyridin-3-yl)-meth-(E)-ylideneamide, prepared from (R)-2-methylpropane-2-sulfinamide and 5-bromo-4-methyl-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 colorless solid. MS: 305.3 and 307.4 (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-c895099bf914452d8b98634bc38228b5
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260408B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes