Boron tribromide → HCID 178480540, compound

HRID 1507468Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[C:10]1[CH:14]=[C:13]([NH:15][C:16]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])=[N:17][C:18]([C:20]2[C:21]([C:26]([F:29])([F:28])[F:27])=[N:22][N:23]([CH3:25])[CH:24]=2)=[O:19])[NH:12][N:11]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:14]=[C:13]([NH:15][C:16]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])=[N:17][C:18]([C:20]2[C:21]([C:26]([F:29])([F:27])[F:28])=[N:22][N:23]([CH3:25])[CH:24]=2)=[O:19])[NH:12][N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-(((3-(2-Fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)amino)((2-fluorophenyl)amino)methylene)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide (0.168 g, 0.323 mmol) was dissolved in dichloromethane (DCM) (5 mL) and cooled to 0° C. in an ice bath. To the cooled solution was added 1 M BBr3 in DCM (0.485 mL, 0.485 mmol). The reaction mixture was brought to room temperature after 1 hour and the reaction was allowed to continue for 16 hours. Next, the reaction was quenched by the addition of MeOH and then volatiles were evaporated in vacuo. The resulting residue was purified by column chromatography (0-10%, DCM:MeOH) to provide the title compound (32% yield). LCMS (ESI): calc.=505; obs. M+H=506.2. HPLC (Method D): retention time was 2.16 minutes.

Workup

waitto continue for 16 hours
customNext, the reaction was quenched by the addition of MeOH
customvolatiles were evaporated in vacuo
customThe resulting residue was purified by column chromatography (0-10%, DCM:MeOH)

Sources & evidence

ORD record: ord-4cd98a04fafa4ca7a29d6d95a6ee946c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221814B2

Reaction notes

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