3-Fluorobenzoyl chloride → [3-Bromo-5-(3-fluoro-benzoylamino)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 1029089Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([NH2:15])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=[O:22].C(N(CC)C(C)C)(C)C>C(Cl)Cl.Cl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([NH:15][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[C:18]([F:17])[CH:19]=2)=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

(5-Amino-3-bromo-pyridin-2-yl)-carbamic acid tert-butyl ester (50 mg, 0.17 mmol), 3-fluoro-benzoyl chloride (28 mg, 0.17 mmol), and N,N-diisopropylethylamine (0.03 mL, 0.19 mmol) were dissolved in CH2Cl2 (2 mL), and stirred or 1 h at 0° C. The reaction solution was diluted with 1 M HCl/CH2Cl2, and filtered through an Extrelut column. The column was washed with CH2Cl2, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 20 to 70% EtOAc/hexanes to provide of [3-bromo-5-(3-fluoro-benzoylamino)-pyridin-2-yl]-carbamic acid tert-butyl ester (47 mg, 66% yield) as a solid.

Workup

filtrationfiltered through an Extrelut column
washThe column was washed with CH2Cl2
concentrationthe filtrate was concentrated
customThe crude product was purified via Biotage
washeluting with a gradient of 20 to 70% EtOAc/hexanes

Sources & evidence

ORD record: ord-670f3d0a4dc941048b74f99574e6ef43
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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