6-Bromoindole → HCID 58107442, compound
Reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[F:16][C:17]1[CH:28]=[CH:27][C:20]([C:21](N(OC)C)=[O:22])=[CH:19][C:18]=1[S:29](=[O:32])(=[O:31])[NH2:30]>O1CCCC1>[F:16][C:17]1[CH:28]=[CH:27][C:20]([C:21]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][CH:3]=2)=[O:22])=[CH:19][C:18]=1[S:29]([NH2:30])(=[O:32])=[O:31]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
A solution of 0.997 g of 6-bromoindole in tetrahydrofuran (20 mL) is cooled to −50° C. and treated by slow addition of 8.79 mL of tert-butyllithium (1.5 M in pentane). After 2 h at −50° C. the reaction mixture is treated with 0.4 g of 4-fluoro-N-methoxy-N-methyl-3-sulfamoyl-benzamide in tetrahydrofuran (10 mL), stirred for an additional 3 h at −50° C. and quenched by addition of 2 mL of saturated aqueous ammonium chloride. The reaction mixture is taken up in ethyl acetate, washed with a saturated sodium chloride solution and dried (magnesium sulfate). After concentration in vacuo the residue is purified by silica gel chromatography (1:1 hexanes/ethyl acetate) to give 2-fluoro-5-(1H-indole-6-carbonyl)-benzenesulfonamide as an amorphous solid. MS (m/z): 317 (M−1); Rf 0.32 (1:1 hexanes/ethyl acetate).
Workup
- customquenched by addition of 2 mL of saturated aqueous ammonium chloride
- washwashed with a saturated sodium chloride solution
- dry with materialdried (magnesium sulfate)
- concentrationAfter concentration in vacuo the residue
- customis purified by silica gel chromatography (1:1 hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-c2141125d8664548926686cd6a883ae5
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975439B2
Reaction notes
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