Methyl vinyl sulfone → 9-Benzenesulfonyl-3-bromo-5-[1-(2-methanesulfonylethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60326

Reaction equation

HRID 60326 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:26]#[N:27])=[C:18]([O:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:13]=3[C:12]3[CH:28]=[C:29]([Br:32])[CH:30]=[N:31][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:33]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH2:34]>CO>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:26]#[N:27])=[C:18]([O:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:34][CH2:33][S:35]([CH3:38])(=[O:37])=[O:36])[CH2:22][CH2:21]4)[C:13]=3[C:12]3[CH:28]=[C:29]([Br:32])[CH:30]=[N:31][C:11]2=3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 670274629-benzenesulfonyl-3-bromo-5-(piperidin-4-yloxy)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 583650969-Benzenesulfonyl-3-bromo-5-[1-(2-methanesulfonylethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 9-benzenesulfonyl-3-bromo-5-(piperidin-4-yloxy)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (400 mg, 0.78 mmol) in methanol (10 mL) was added methyl vinyl sulfone (207 mg, 1.95 mmol). The resultant reaction stirred at ambient temperature for 24 hours, then concentrated in-vacuo. The residue was triturated with ethyl acetate to afford the title compound as a pale yellow solid (446 mg, 92%). 1H NMR (300 MHz, DMSO-d6): 9.46 (d, J=0.4 Hz, 1H), 8.90 (d, J=2.2 Hz, 1H), 8.67 (d, J=2.3 Hz, 1H), 8.24-8.24 (m, 2H), 7.78 (t, J=7.4 Hz, 1H), 7.64 (t, J=7.8 Hz, 2H), 4.86-4.86 (m, 1H), 3.27 (t, J=7.1 Hz, 2H obscured solvent peak), 3.03 (s, 3H), 2.92-2.80 (m, 2H), 2.73 (t, J=6.8 Hz, 2H), 2.21 (t, J=10.9 Hz, 2H), 2.22-1.98 (m, 2H), 1.92-1.92 (m, 2H).

Workup

  1. customThe resultant reaction
  2. concentrationconcentrated in-vacuo
  3. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-e28b2456b918421bb6e8f7cc2e744795
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Linked notes

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