5-Bromoindole → 2-(1H-Indol-5-yl)-N,N-dimethylethenesulphonamide

HRID 982005Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][N:12]([CH3:18])[S:13]([CH:16]=[CH2:17])(=[O:15])=[O:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([CH:17]=[CH:16][S:13]([N:12]([CH3:18])[CH3:11])(=[O:15])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-bromoindole (7.7 g), N,N-dimethylethenesulphonamide (5.3 g) triethylamine (15 ml), acetonitrile (5 ml), palladium (II) acetate (0.35 g) and tri-o-tolylphosphine (0.95 g) was heated at 100° C. in an autoclave for 3 h. The resulting cooled mixture was partitioned between hydrochloric acid (2N, 300 ml) and ethyl acetate (2×150 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by `flash` chromatography (V, 7 cm col.) to give the title compound as a crystalline solid (3.8 g) m.p. 148°-150° C.

Workup

temperatureThe resulting cooled mixture
customwas partitioned between hydrochloric acid (2N, 300 ml) and ethyl acetate (2×150 ml)
dry with materialThe combined extracts were dried (Na2SO4)
customevaporated in vacuo
customThe residue was purified by `flash` chromatography (V, 7 cm col.)

Sources & evidence

ORD record: ord-d0ff7951d44f4785957f6658ff277433
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994483

Reaction notes

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