Pivaloyl chloride → Methyl 2-chloro-4-fluoro-3-(pivalamidomethyl)benzoate

HRID 1469791Notes

Reaction equation

HRID 1469791 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([Cl:14])=[C:5]([CH:10]=[CH:11][C:12]=1[F:13])[C:6]([O:8][CH3:9])=[O:7].CCN(C(C)C)C(C)C.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[Cl:14][C:4]1[C:3]([CH2:2][NH:1][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:12]([F:13])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 86692270Methyl 3-(aminomethyl)-2-chloro-4-fluorobenzoate

Product 1

HCID 86692269Methyl 2-chloro-4-fluoro-3-(pivalamidomethyl)benzoateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in step-2 of Intermediate-2 using methyl 3-(aminomethyl)-2-chloro-4-fluorobenzoate (340 mg, 1.42 mmol), DIPEA (550 mg, 4.27 mmol) and pivaloyl chloride (204 mg, 1.7 mmol) in CH2Cl2 (5 mL) to afford 350 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 7.81-7.74 (m, 2H), 7.36-7.30 (t, J=9.0 Hz, 1H), 4.39-4.37 (d, J=4.5 Hz, 2H), 3.85 (s, 3H), 1.06 (s, 9H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-bbfd4163399c449292ae76c8e378f993
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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