Aniline → HCID 57742714、化合物

HRID 911878ノート

反応式

HRID 911878 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:14][C:15]1[CH:16]=[C:17]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH2:27]Cl)[N:26]=2)=[N:19][CH:20]=1>CN1C(=O)CCC1>[Br:14][C:15]1[CH:16]=[C:17]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:18]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH2:27][NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:26]=2)=[N:19][CH:20]=1

参加物

5

反応物 3

HCID 6115AnilineHCID 10796Cesium carbonateHCID 57742594HCID 57742594、化合物

生成物 1

HCID 57742714HCID 57742714、化合物収率 29.2%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

Aniline (0.0352 g, 0.378 mmol) was dissolved in 2 mL NMP at ambient temperature. Cs2CO3 (0.0246 g, 0.0756 mmol) and solid 5-bromo-N-(4-(chloromethyl)thiazol-2-yl)-3-phenoxypyridin-2-amine (0.030 g, 0.0756 mmol) were 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 (0.010 g, 29.2% yield) as tan solids. 1H NMR (CDCl3) δ 4.34 (br s, 3H), 6.67-6.74 (m, 4H), 7.07 (d, J=8.0 Hz, 2H), 7.13 (d, J=1.8 Hz, 1H), 7.18 (t, J=7.7 Hz, 2H), 7.24-7.27 (m, 1H), 7.43 (t, J=7.9 Hz, 2H), 8.13 (d, J=1.6 Hz, 1H), 8.74 (br s, 1H).

後処理

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-d0ae3af195f14bae924e856133acf28a
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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