Diisopropylethylamine → 2,6-difluoro-N-(5-(2-methyl-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)pyridin-2-yl)benzamide

HRID 2272247Notes

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[S:17][C:16]2[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=2[C:14]=1[C:22]1[CH:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=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:28][C:25]1[CH:24]=[CH:23][C:22]([C:14]2[C:15]3[CH2:21][CH2:20][CH2:19][CH2:18][C:16]=3[S:17][C:13]=2[CH3:12])=[CH:27][N:26]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (9.4 mg, 53 μmol) was added to a stirred solution of 240 (6.5 mg, 26 μmol) and Hünig's base (28 μL, 21 mg, 0.2 mmol) in dichloromethane (0.5 mL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (0.6 mL), methanol (0.4 mL) and 2 M sodium hydroxide solution (0.2 mL). The mixture was stirred and heated to 60° C. for 5 min then cooled to room temperature, diluted with dichloromethane (5 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-20% ethyl acetate in hexane) provided 236 (5.1 mg, 50%) as a solid: LRESIMS m/z 385.1 [M+H]+, calcd. for C21H19F2N2O1S1 385.1.

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-d6ffce322f444b91b1f112a61fa78f81
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120751B2

Reaction notes

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