Sodium borohydride → HCID 58731274, compound

HRID 2046549Notes

Reaction equation

HRID 2046549 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9](=[O:10])[CH2:8][S:7][C:6]=2[CH:11]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]([OH:10])[CH2:8][S:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58731164HCID 58731164, compound

Product 1

HCID 58731274HCID 58731274, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In analogy to the procedures described for the preparation of intermediate A-8 [A], intermediates A-2 [B] and A-2 [C], 6-bromo-benzo[b]thiophen-3-one was reacted with sodium borohydride in ethanol to give (rac)-6-bromo-2,3-dihydro-benzo[b]thiophen-3-ol, which was subsequently reacted with diphenylphosphoryl azide, DBU in toluene to give (rac)-3-azido-6-bromo-2,3-dihydro-benzo[b]thiophene, which was then reduced with triphenylphosphine in THF/water to yield the title compound as light yellow oil. MS: 229 (M+, 1Br).

Workup

  1. customIn analogy to the procedures described for the preparation of intermediate

Sources & evidence

ORD record
ord-628409a539c4410b952309f023a32881
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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