Diisopropylethylamine → HCID 54596274, compound

HRID 530786Notes

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].[Br:12][C:13]1[C:14]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)=[CH:15][C:16]2[O:20][CH2:19][O:18][C:17]=2[CH:21]=1.CCN(C(C)C)C(C)C>ClCCl.O1CCCC1.CO.[OH-].[Li+]>[Br:12][C:13]1[C:14]([C:22]2[CH:23]=[CH:24][C:25]([NH:26][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=3[F:11])=[CH:27][CH:28]=2)=[CH:15][C:16]2[O:20][CH2:19][O:18][C:17]=2[CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (113 mg, 640 μmol) was added to a stirred solution of 80 (125 mg, 430 μmol) and Hünig's base (224 μL, 166 mg, 1.28 mmol) in dichloromethane (2.1 mL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (2 mL), methanol (2 mL) and 1.2 M lithium hydroxide solution (1 mL). The mixture was stirred and heated to 60° C. for 5 min then cooled to room temperature, diluted with dichloromethane and dried with sodium sulfate. The mixture was concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 81 (99.2 mg, 54%) as a solid: LRESIMS m/z 432.0 [M+H]+, calcd. for C20H13Br1F2N1O3 432.0.

Workup

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

Sources & evidence

ORD record: ord-5e87d2778d654e76a8cffb951f116566
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353099B2

Reaction notes

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