Phenol → HCID 57742823、化合物

HRID 911877ノート

反応式

HRID 911877 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:10][C:11]1[CH:12]=[C:13]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:14]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH2:23]Cl)[N:22]=2)=[N:15][CH:16]=1>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:14]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH2:23][O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:22]=2)=[N:15][CH:16]=1

参加物

5

反応物 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 57742594HCID 57742594、化合物

生成物 1

HCID 57742823HCID 57742823、化合物収率 20.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Phenol (0.0356 g, 0.378 mmol) was dissolved in 3 mL THF at ambient temperature. NaH (0.00907 g, 0.378 mmol) was added and the mixture stirred for 30 minutes at ambient temperature. Solid N-(5-Bromo-3-phenoxypyridin-2-yl)-4-(chloromethyl)thiazol-2-amine (0.030 g, 0.0756 mmol) (Example 322) was then added to the reaction and the mixture was stirred at ambient temperature overnight. The reaction was concentrated to dryness, dissolved in CH2Cl2, washed with water, dried over Na2SO4, and concentrated to dryness. The residue was purified by preparative HPLC to give the title compound (0.007 g, 20.4% yield) as the least polar of the two major products. 1H NMR (CDCl3) δ 5.07 (s, 2H), 6.88 (s, 1H), 6.96 (t, J=7.3 Hz, 1H), 7.01 (d, J=8.0 Hz, 2H), 7.07 (d, J=8.8 Hz, 2H), 7.14 (d, J=2.0 Hz, 1H), 7.23-7.31 (m, 3H), 7.43 (t, J=8.0 Hz, 2H), 8.14 (d, J=2.0 Hz, 1H), 8.76 (br s, 1H).

後処理

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. concentrationThe reaction was concentrated to dryness
  3. dissolutiondissolved in CH2Cl2
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-156a254cd1e84ee5a314448ecbf12104
出典データセット
uspto-grants-2011_09
特許番号
US08022223B2

反応ノート

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