Diisopropylethylamine → HCID 58486771, compound

HRID 874600Notes

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[N:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=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>CN(C1C=CN=CC=1)C.ClCCl.O1CCCC1.CO.[OH-].[Li+]>[Br:12][C:13]1[C:14]([C:22]2[N:23]=[CH:24][C:25]([NH:28][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=3[F:11])=[N:26][CH:27]=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 (8.6 mg, 48 μmol) was added to a stirred solution of 15 (9.5 mg, 32 μmol), Hünig's base (17 μL, 13 mg, 97 μmol), and DMAP (1 mg, 8 μmol) in dichloromethane (200 μL) at room temperature. The reaction was stirred for 25 min. The solution was diluted with tetrahydrofuran (750 μL), methanol (500 μL) and 1.2 M lithium hydroxide solution (250 μL). The mixture was stirred and heated to 60° C. for 10 min then cooled to room temperature and diluted with dichloromethane (5 mL) and dried with sodium sulfate. The mixture was concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 16 (9.3 mg, 66%) as a solid: LRESIMS m/z 434.0 [M+H]+, calcd. for C18H11Br1F2N3O3 434.0.

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-7ff5c6df1f2d46b8b4acb31fddb02938
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980629B2

Reaction notes

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