Tetrabutylammonium Fluoride → (Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one

HRID 20692ノート

反応式

HRID 20692 の反応式
[Si]([O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][O:13][C:14]1[C:15]([O:34][CH3:35])=[CH:16][CH:17]=[C:18]2[C:23]=1[O:22][C:21](=[O:24])[CH:20]=[C:19]2[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=1[Cl:33])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[Cl:33][C:27]1[CH:28]=[N:29][CH:30]=[C:31]([Cl:32])[C:26]=1[NH:25][C:19]1[C:18]2[C:23](=[C:14]([O:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][OH:8])[C:15]([O:34][CH3:35])=[CH:16][CH:17]=2)[O:22][C:21](=[O:24])[CH:20]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 86618136HCID 86618136、化合物

生成物 1

HCID 24849220(Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of (Z)-8-(4-(tert-butyldimethylsilyloxy)but-2-enyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one and TBAF (2 mL, 2M THF) was maintained at rt for 18 h, poured into water, and then extracted with EtOAc. The extract was dried, filtered, concentrated, and purified by reverse-phase HPLC (25→100% MeCN/H2O) to give (Z)-4-(3,5-dichloropyridin-4-ylamino)-8-(4-hydroxybut-2-enyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, CD3OD-d6): δ 8.71 (s, 2H), 7.85 (d, 1H), 7.18 (d, 1H), 7.83 (m, 2H), 4.77 (m, 3H), 4.15 (d, 2H), 4.01 (s, 3H); MS (ESI): 422.8.

後処理

  1. extractionextracted with EtOAc
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (25→100% MeCN/H2O)

出典と根拠

ORDレコード
ord-ac62aebc72e9427e9373a00eff9e5822
出典データセット
uspto-grants-2010_06
特許番号
US07745646B2

反応ノート

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