Hydrogen Bromide → 3-(3,5-Difluorophenyl)-5-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331384Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=3)[C:11](=[O:20])[C:10]=2[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.Br.[OH-].[Na+]>CC(O)=O>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=3)[C:11](=[O:20])[C:10]=2[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3-(3,5-difluorophenyl)-5-methoxy-2-(pyridin-3-yl)-1H-inden-1-one (210 mg, 0.60 mmol) obtained in Step 4 in AcOH (6 mL) was added HBr (3 mL). The mixture was heated to reflux at 120° C. for 16 h. The reaction mixture was cooled to room temperature and neutralized with 3N—NaOH. The resulting solution was extracted with EtOAc (10 mL). The extracts were washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by recrystallization with CH2Cl2/hexanes to afford the desired product (200 mg, 99%).

Workup

temperatureThe mixture was heated
extractionThe resulting solution was extracted with EtOAc (10 mL)
washThe extracts were washed with H2O and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by recrystallization with CH2Cl2/hexanes

Sources & evidence

ORD record: ord-1ff52a3c09cd4beb9d64f0880d28626c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877747B2

Reaction notes

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