Toluene → 4-(7-(6-chloropyridin-3-yloxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamide

HRID 1676326ノート

反応式

HRID 1676326 の反応式
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].[Cl:14][C:15]1[N:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[CH:28]=[C:29](I)[S:30][C:23]=23)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(Cl)Cl.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[Cl:14][C:15]1[N:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[CH:28]=[C:29]([C:8]4[CH:9]=[CH:10][C:5]([C:3]([NH:2][CH3:1])=[O:4])=[CH:6][CH:7]=4)[S:30][C:23]=23)=[CH:17][CH:16]=1

参加物

9

反応物 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 866146527-(6-Chloropyridin-3-yloxy)-2-iodothieno[3,2-b]pyridine

生成物 1

HCID 589494324-(7-(6-chloropyridin-3-yloxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamide収率 65.2%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
85 °C

実験手順

A stirred mixture of 4-(methylcarbamoyl)phenylboronic acid (0.112 g, 0.625 mmol), 7-(6-chloropyridin-3-yloxy)-2-iodothieno[3,2-b]pyridine (0.194 g, 0.50 mmol), cesium carbonate (0.244 g, 0.750 mmol), toluene (4 mL) and EtOH (1 mL) was sparged with nitrogen for 5 minutes and then Pd(PPh3)4 (0.0347 g, 0.0300 mmol) was added. The reaction was heated to 85° C. for 5 hours in a sealed vessel. The mixture was diluted with DCM (20 mL) and water (20 mL). The phases were separated, and the organic was dried (Na2SO4), filtered, and concentrated in vacuo. The crude was purified by preparative TLC (2 mm thickness, Rf=0.36) eluting with 10% MeOH/CHCl3. The product was obtained as a solid (129 mg, 59%). HPLC: 98% purity (220 nm); LRMS (ESI+): 97% purity, 220 nm, m/z 396 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 8.55 (d, J=6 Hz, 1H), 8.36 (d, J=3 Hz, 1H), 7.85 (m, 2H), 7.79 (m, 3H), 7.53 (d, J=9 Hz, 1H), 7.44 (d, J=9 Hz, 1H), 6.59 (d, J=6 Hz, 1H), 6.41 (br d, J=5 Hz, 1H), 3.05 (d, J=5 Hz, 3H).

後処理

  1. customwas sparged with nitrogen for 5 minutes
  2. customThe phases were separated
  3. dry with materialthe organic was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by preparative TLC (2 mm thickness, Rf=0.36)
  7. washeluting with 10% MeOH/CHCl3

出典と根拠

ORDレコード
ord-983ba91aad74404388bb5124b6172bac
出典データセット
uspto-grants-2011_08
特許番号
US08003662B2

反応ノート

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