Pivaloyl chloride → Methyl 2-chloro-4-fluoro-5-(pivalamidomethyl)benzoate

HRID 1469789Notes

Reaction equation

HRID 1469789 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:14])=[CH:5][C:6]([Cl:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].CCN(C(C)C)C(C)C.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[Cl:13][C:6]1[CH:5]=[C:4]([F:14])[C:3]([CH2:2][NH:1][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 86692267Methyl 5-(aminomethyl)-2-chloro-4-fluorobenzoate

Product 1

HCID 86692266Methyl 2-chloro-4-fluoro-5-(pivalamidomethyl)benzoateYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in step-2 of Intermediate-2 using methyl 5-(aminomethyl)-2-chloro-4-fluorobenzoate (180 mg, 0.83 mmol), DIPEA (321 mg, 2.49 mmol) and pivaloyl chloride (120 mg, 1.0 mmol) in CH2Cl2 (5 mL) to afford 250 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.16 (t, 1H), 7.73 (d, J=6.9 Hz, 1H), 7.58-7.54 (d, J=10.2 Hz, 1H), 4.26-4.24 (d, J=5.7 Hz, 2H), 3.83 (s, 3H), 1.11 (s, 9H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0fd3e6b8883b4fb48c5c8a652c059998
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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