Tributylphosphine → Ethyl 7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

HRID 1188888ノート

反応式

HRID 1188888 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[C:27]([Si:31]([C:43]([CH3:46])([CH3:45])[CH3:44])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[O:32][CH2:33][CH:34](O)[CH3:35])([CH3:30])([CH3:29])[CH3:28].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:43]([Si:31]([C:27]([CH3:28])([CH3:30])[CH3:29])([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[O:32][CH2:33][CH:34]([CH3:35])[O:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2)([CH3:44])([CH3:45])[CH3:46]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 66726144Ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylateHCID 668862121-{[Di-tert-butyl(phenyl)silyl]oxy}propan-2-ol

生成物 1

HCID 67118494Ethyl 7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate収率 60.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A mixture of ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (2.3 g), 1-{[di-tert-butyl(phenyl)silyl]oxy}propan-2-ol (3.9 g), 1,1′-(azodicarbonyl)dipiperidine (3.1 g), tributylphosphine (3.1 mL) and tetrahydrofuran (20 mL) was stirred at 50° C. for 18 hr. The reaction solution was allowed to cool to room temperature, and the precipitated white solid was filtered off. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=0:100 to 30:70, volume ratio) to give the title compound (2.4 g, yield 57%) as an orange oil. MS 672 (MH+).

後処理

  1. temperatureto cool to room temperature
  2. filtrationthe precipitated white solid was filtered off
  3. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-d2e18b7c6f984c28a0feffc05293c6e5
出典データセット
uspto-grants-2014_03
特許番号
US08673942B2

反応ノート

読み込み中…