Benzenesulfonamide, 4-amino-N,N-dimethyl- → 5-(Oxazol-5-yl)-1,3-dihydroindol-2-one

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Reaction Steps

3-Methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 4-oxazol -5-yl-aniline according to Procedure D: 1H NMR (DMSO-d6): δ 10.7 (s, 1H), 8.3 (s, 1H), 7.5 (s, 3H), 6.9 (d, 1H), 4.5 (s, 1H), 2.0 (s, 3H); APCI−MS m/z 247 (M+H)+. 5-Oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 3-methylsulfanyl-5oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure D: 1H NMR (DMSO-d6): δ 10.5 (s, 1H), 8.3 (s, 1H), 7.5 (m, 3H), 6,8 (d, 1H), 3.5 (s, 2H); APCI−MS m/z 201 (M+H)+. 3-Ethoxymethylene-5oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 5-oxazol-5-yl-1,3-dihydroindol-2-one according to Procedure I: 1H NMR (DMSO-d6): δ 10.43 (s, 1H), 8.37 (s, 1H), 7.76 (s, 1H), 7.51 (m, 2H), 6.90, (d, 1H), 4.43 (q, 2H), 1.4 (t, 3H): APCI−MS m/z 255 (M−H)+. The title compound was prepared in 36% yield from 3-ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one and N,N-dimethyl4-aminobenzenesulfonamide according to Procedure J: 1H NMR (DMSO-d6): δ 10.9 ( d, 1H), 10.8 (s, 1H), 8.8 (d, 1H), 8.4 (s, 1H), 8.0 (s, 1H), 7.7 (br d, 4H), 7.5 (m, 2H), 7.0 (d, 1H), 2.6 (s, 6H); APCI−MS m/z 409 (M−H)−.

Provenance & Evidence