Diisopropylethylamine → 2,6-difluoro-N-(5-(2-methylbenzofuran-3-yl)pyridin-2-yl)benzamide

HRID 2272249Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[CH3:12][C:13]1[O:14][C:15]2[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=2[C:17]=1[C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=1.CCN(C(C)C)C(C)C>ClCCl.O1CCCC1.CO.[OH-].[Na+]>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]2[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[O:14][C:13]=2[CH3:12])=[CH:23][N:22]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (47 mg, 0.3 mmol) was added to a stirred solution of 245 (30 mg, 0.1 mmol) and Hünig's base (140 μL, 104 mg, 0.8 mmol) in dichloromethane (1.0 mL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (0.8 mL), methanol (0.6 mL) and 2 M sodium hydroxide solution (0.2 mL). The mixture was stirred and heated to 60° C. for 15 min then cooled to room temperature, diluted with dichloromethane (10 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-20% ethyl acetate in hexane) provided 246 (35.5 mg, 73%) as a solid: LRESIMS m/z 365.1 [M+H]+, calcd. for C21H15F2N2O2 365.1.

Workup

stirringThe mixture was stirred
temperaturethen cooled to room temperature
dry with materialdried with sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d9d18c73237042ddb3aa15dcd5c913da
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120751B2

Reaction notes

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