Ammonia → HCID 136097738, compound

HRID 1662269Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([NH2:35])=[N:5][C:6]2([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[C:23]([C:29]2[CH:34]=[N:33][CH:32]=[CH:31][N:30]=2)[CH:22]=1)[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1.B(Br)(Br)Br.O.N>C(Cl)Cl>[NH2:35][C:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])[C:6]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:29]3[CH:34]=[N:33][CH:32]=[CH:31][N:30]=3)[CH:22]=2)([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[N:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-fluoro-1-(4-methoxy-3-(pyrazin-2-yl)phenyl)-1-(2-(trifluoromethyl) pyridin-4-yl)-1H-isoindol-3-amine (0.65 g, 1.36 mmol) in DCM (12.5 ml), boron tribromide (0.718 ml, 4.20 mmol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 1 hour and then allowed to reach room temperature. Water (5 ml) was added and the pH was adjusted to approx 8 with aqeuous conc. NH3. The organic phase was separated and aqueous phase was extracted with DCM (20 mL). The combined organic phases were passed through a phase separator (Sorbent) and concentrated under reduced pressure. The residue was purified twice by preparative chromatography to give the title compound (210 mg, 32%).

Workup

customto reach room temperature
customThe organic phase was separated
extractionaqueous phase was extracted with DCM (20 mL)
concentrationconcentrated under reduced pressure
customThe residue was purified twice by preparative chromatography

Sources & evidence

ORD record: ord-406b9c996d5d43918ef6c96a8db9df32
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030500B2

Reaction notes

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