Stannane, tributyl(1-ethoxyethenyl)- → 4-(3-chloro-5-(1-ethoxyvinyl)pyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

HRID 20644

反応式

HRID 20644 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:28])[C:7]=1[NH:8][C:9]1[C:18]2[C:13](=[C:14]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[O:12][C:11](=[O:27])[CH:10]=1.C([Sn](CCCC)(CCCC)[C:34]([O:36][CH2:37][CH3:38])=[CH2:35])CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:28][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:34]([O:36][CH2:37][CH3:38])=[CH2:35])[C:7]=1[NH:8][C:9]1[C:18]2[C:13](=[C:14]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[O:12][C:11](=[O:27])[CH:10]=1

参加物

5

反応物 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 248494324-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

生成物 1

HCID 248494754-(3-chloro-5-(1-ethoxyvinyl)pyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (0.206 g, 0.441 mmol, Example 11), PdCl2(PPh3)2 (31 mg, 0.044 mmol), tributyl(1-ethoxyvinyl)tin (0.20 mL, 0.57 mmol), and toluene (5 mL) was heated at 80° C. under N2 for 4 h. After allowing to cool to rt, the mixture was filtered through Celite and washed with EtOAc. The filtrate was washed with aqueous KF, dried, filtered, concentrated, and purified by silica gel chromatography (0→50% EtOAc/hexanes) to give 4-(3-chloro-5-(1-ethoxyvinyl)pyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.19 (s, 1H), 8.80 (s, 1H), 8.65 (s, 1H), 7.94 (d, 1H), 7.16 (d, 1H), 4.83 (m, 1H), 4.53 (m, 2H), 4.41 (d, 1H), 3.90 (s, 3H), 3.61 (m, 2H), 1.85-1.52 (m, 8H), 0.89 (t, 3H); MS (ESI): 457.1.

後処理

  1. temperatureto cool to rt
  2. filtrationthe mixture was filtered through Celite
  3. washwashed with EtOAc
  4. washThe filtrate was washed with aqueous KF
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (0→50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ddc9b5bf070a45d4b17954f779411030
出典データセット
uspto-grants-2010_06
特許番号
US07745646B2

関連ノート

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