Triethylamine → Methyl 5-bromo-2-(2-(4-cyanophenoxy)acetamido)benzoate

HRID 520834Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][C:21](Cl)=[O:22])=[CH:17][CH:16]=1)#[N:14].C(N(CC)CC)C>ClCCl>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:21](=[O:22])[CH2:20][O:19][C:18]2[CH:24]=[CH:25][C:15]([C:13]#[N:14])=[CH:16][CH:17]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-amino-5-bromobenzoate (4.0 g, 17.39 mmol) in dichloromethane (60 mL) was added 2-(4-cyanophenoxy)acetyl chloride (3.74 g, 19.13 mmol, Intermediate 2: step a) to form a thick suspension. An additional 30 mL of dichloromethane was added. The reaction was then cooled to 0° C. and triethylamine (5.32 mL, 38.25 mmol) was added dropwise. The cold bath was removed and the reaction was stirred at room temperature for 2 hours, then filtered to give the title compound as a white solid. The filtrate was washed with water, followed by saturated aqueous NH4Cl solution. The organic layer was dried (MgSO4), filtered, concentrated, and the residue was purified by flash column chromatography (silica gel, 20% EtOAc-heptane) to afford more of the title compound.

Workup

customstep a) to form a thick suspension
customThe cold bath was removed
filtrationfiltered

Sources & evidence

ORD record: ord-3a118594e5f545bab24dbba9266820d9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328095B2

Reaction notes

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