Chlorotrimethylsilane → 2-(5-Fluorobenzo[b]thiophen-2-yl)ethanamine

HRID 1843961Notes

Reaction equation

HRID 1843961 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7](/[CH:9]=[CH:10]/[N+:11]([O-])=O)=[CH:8][C:4]=2[CH:3]=1.[Li+].[BH4-].C[Si](Cl)(C)C>C1COCC1>[F:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]([CH2:9][CH2:10][NH2:11])=[CH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 66801961(E)-5-fluoro-2-(2-nitrovinyl)benzo[b]thiophene

Product 1

HCID 668018432-(5-Fluorobenzo[b]thiophen-2-yl)ethanamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using analogous conditions and workup as described for the preparation of I-14b above, (E)-5-fluoro-2-(2-nitrovinyl)benzo[b]thiophene (I-50d: 1.2 g, 5.375 mmol) was reacted with LiBH4 (468.34 mg, 21.503 mmol), trimethylsilyl chloride (4.649 g, 43 mmol) and THF (50 mL) to afford 1 g of the product (100% yield). LCMS: 98.10%, m/z=196.0 (M+1)

Sources & evidence

ORD record
ord-ce5fc9033b99442a91ad155dff4f185f
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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