HCID 67228991、化合物 → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515686ノート

反応式

HRID 1515686 の反応式
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][O:27][CH3:28])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][O:27][CH3:28])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 1

HCID 67228991HCID 67228991、化合物

生成物 1

HCID 532510852-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine収率 19.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (411 mg, 1.09) and 10% palladium on activated carbon (100 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 6 h. The mixture was cooled to room temperature before The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo and purified using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (80 mg, 19.4%) as a white solid: LC/MS m/e calcd for C23H28N2O3S [M+H]+ 413.56, observed 413.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.30 (s, 1H), 8.20 (s, 1H), 7.89-7.93 (m, J=8.3 Hz, 2H), 7.55-7.66 (m, 2H), 6.67 (s, 1H), 4.61 (s, 2H), 4.37 (t, J=8.0 Hz, 1H), 3.33-3.48 (m, 3H), 3.08-3.13 (m, 3H), 2.25-2.33 (m, 1H), 2.12-2.20 (m, 1H), 1.61-1.88 (m, 5H), 1.45-1.56 (m, 2H), 1.18-1.31 (m, 2H).

後処理

  1. temperatureThe mixture was cooled to room temperature before The catalyst
  2. customwas removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified

出典と根拠

ORDレコード
ord-b3ea1737d637441ba7aa08a200207cc1
出典データセット
uspto-grants-2012_07
特許番号
US08222416B2

反応ノート

読み込み中…