Isobutyryl chloride → Ethyl 6-chloro-2-fluoro-3-(isobutyramidomethyl)benzoate

HRID 1469787Notes

Reaction equation

HRID 1469787 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:15])=[C:5]([C:11]([Cl:14])=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:16](Cl)(=[O:20])[CH:17]([CH3:19])[CH3:18].CCN(C(C)C)C(C)C>C1COCC1>[Cl:14][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:15])[C:3]([CH2:2][NH:1][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 58483233Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate

Product 1

HCID 86692264Ethyl 6-chloro-2-fluoro-3-(isobutyramidomethyl)benzoateYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described in Intermediate-2, step-2 using ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate (Intermediate-2, step-1, 1.00 g, 4.32 mmol), isobutyryl chloride (690 mg, 6.48 mmol) and DIPEA (1.67 g, 12.96 mmol) in THF (30 mL) to afford 1.0 g of the title product.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c29d800a3fc84559b971f350d067a031
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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