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

反応式

HRID 60326 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e28b2456b918421bb6e8f7cc2e744795
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

関連ノート

読み込み中…