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

HRID 60327
ノート
印刷プレビュー

反応式

HRID 60327 の反応式
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:32]#[N:33])=[C:18]([O:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:22][CH2:21]4)[C:13]=3[C:12]3[CH:34]=[C:35](Br)[CH:36]=[N:37][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C>[Pd].ClCCl>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:32]#[N:33])=[C:18]([O:19][CH:20]4[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:25]4)[C:13]=3[C:12]3[CH:34]=[CH:35][CH:36]=[N:37][C:11]2=3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 8471TriethylamineHCID 583650969-Benzenesulfonyl-3-bromo-5-[1-(2-methanesulfonylethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

生成物 1

HCID 583651709-Benzenesulfonyl-5-[1-(2-methanesulfonylethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile収率 66.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 6344
Dichloromethane
溶媒

実験手順

A suspension of 9-benzenesulfonyl-3-bromo-5-[1-(2-methanesulfonyl-ethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (245 mg, 0.39 mmol) and palladium on carbon (10 wt %, 50 mg) in industrial methylated spirits (5 mL), dichloromethane (5 mL), and triethylamine (3 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 24 hours. The reaction vessel was purged with nitrogen then the reaction mixture was filtered through a PTFE filter cup. The filtrate was evaporated in-vacuo and the resultant residue purified by flash chromatography (silica, 10 g column, ISCO, 0-50% ethyl acetate in dichloromethane) to afford the title compound as an off-white solid (140 mg, 65%). LCMS (Method C): RT=4.97 min, M+H+=400. 1H NMR (300 MHz, DMSO-d6): 9.49 (s, 1H), 8.76 (dd, J=4.8, 1.6 Hz, 1H), 8.63 (dd, J=7.9, 1.7 Hz, 1H), 8.25-8.24 (m, 2H), 7.76 (t, J=7.4 Hz, 1H), 7.64-7.63 (m, 3H), 4.76-4.75 (m, 1H), 3.26 (t, J=7.4 Hz, 2H obscured by solvent peak), 3.02 (s, 3H), 2.88 (d, J=11.3 Hz, 2H), 2.72 (t, J=6.8 Hz, 2H), 2.14-2.14 (m, 4H), 1.91-1.91 (m, 2H).

後処理

  1. customThe reaction vessel was purged with nitrogen
  2. filtrationthe reaction mixture was filtered through a PTFE
  3. filtrationfilter cup
  4. customThe filtrate was evaporated in-vacuo
  5. customthe resultant residue purified by flash chromatography (silica, 10 g column, ISCO, 0-50% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-05d08099f5bb46818e3795081ca9d370
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09440976B2

反応ノート

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