Divinyl sulfone → HCID 46834657, compound

HRID 661977Notes

Reaction equation

HRID 661977 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])=[CH:8][CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[CH:25]([S:27]([CH:30]=[CH2:31])(=[O:29])=[O:28])=[CH2:26]>CC(O)C>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:7]1[C:6]2[C:5]3[C:13](=[CH:14][C:2]([N:1]4[CH2:31][CH2:30][S:27](=[O:29])(=[O:28])[CH2:25][CH2:26]4)=[CH:3][CH:4]=3)[NH:12][C:11]=2[C:10]([C:15]([NH2:17])=[O:16])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6496Divinyl sulfoneHCID 59375160HCID 59375160, compound

Product 1

HCID 46834657HCID 46834657, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7-amino-4-(2-fluorophenyl)-9H-carbazole-1-carboxamide (Example 54-1, 36 mg, 0.113 mmol) in 2-propanol (1.0 mL) was treated with vinylsulfonylethene (20 μL, 0.199 mmol) at rt. The reaction mixture was heated at 100° C. for 26 h. The mixture was cooled to rt, concentrated and the residue was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-(1,1-dioxothiomorpholino)-9H-carbazole-1-carboxamide as a yellow solid (14 mg, 28%). 1H NMR (400 MHz, DMSO-d6) δ 11.26 (1H, s), 8.17 (1H, br. s.), 7.90 (1H, d, J=7.9 Hz), 7.47-7.62 (3H, m), 7.37-7.46 (2H, m), 7.35 (1H, d, J=1.8 Hz), 7.01 (1H, d, J=7.9 Hz), 6.93 (1H, d, J=8.3 Hz), 6.74 (1H, dd, J=9.0, 2.4 Hz), 3.77-3.81 (4H, m), 3.08-3.19 (4H, m). Mass spectrum m/z 438.1 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5d20daadd642466c865636cd60897a84
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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