Boron tribromide → HCID 11605279, compound
Reaction equation
[F:1][C:2]([F:34])([F:33])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24]C)=[CH:21][CH:22]=3)[CH:17]=[C:16]([CH3:26])[C:15]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].B(Br)(Br)Br>C(Cl)Cl>[F:33][C:2]([F:1])([F:34])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([OH:24])=[CH:21][CH:22]=3)[CH:17]=[C:16]([CH3:26])[C:15]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:9][CH:8]=1)(=[O:4])=[O:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Compound 31 (47 mg, 0.10 mmol, 1 equiv) was dissolved in CH2Cl2 (5 mL) and cooled to 0° C. under N2. BBr3 (46 μL, 0.49 mmol, 5 equiv) was added dropwise and the resulting solution was allowed to stir at 0° C. for 4 h. The reaction mixture was then poured into ice and product extracted into EtOAc (250 mL). The organics were washed with saturated aqueous NaCl (100 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by silica gel flash column chomatography (1:1 EtOAc:hexanes) to provide the title compound (32) (30 mg, 66%) as a yellow solid. 1HNMR (400 MHz, DMSO-d6): δ 11.53 (br s, 1H), 10.69 (br s, 1H), 7.88 (m, 1H), 7.60 (m, 1H), 7.27-7.14 (m, 7H), 6.98 (m, 2H), 6.59 (m, 2H), 2.20 (s, 3H). MS m/z 472.3 (M−H)−.
Workup
- additionThe reaction mixture was then poured into ice and product
- extractionextracted into EtOAc (250 mL)
- washThe organics were washed with saturated aqueous NaCl (100 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe residue was purified by silica gel flash column chomatography (1:1 EtOAc:hexanes)
Sources & evidence
- ORD record
- ord-4b0631f3e65d477c86a261ba0c2d5bc2
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07649093B2
Reaction notes
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