Cesium carbonate → HCID 58958594、化合物

HRID 915602

反応式

HRID 915602 の反応式
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1Br)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([C:30]1[CH:34]=[C:33]([NH2:35])[N:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH3:42])[N:31]=1)([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:35][C:33]1[N:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH3:42])[N:31]=[C:30]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:34]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 7706433-tert-Butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine2 回HCID 3731394N,N-dibenzyl-2-bromobenzenesulfonamide

生成物 1

HCID 58958594HCID 58958594、化合物収率 77%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

N,N-Dibenzyl-2-bromobenzenesulfonamide (from Step 1, 333 mg, 0.80 mmol), 3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate C), cesium carbonate (365 mg, 1.12 mmol), Pd2dba3 (41.4 mg, 0.04 mmol), and BINAP (49.8 mg, 0.08 mmol) were dissolved in toluene (7 mL) under nitrogen, and the flask was heated at 110° C. for 20 h. The reaction mixture was cooled to rt, and the solid residue removed by filtration. The solvent was removed under reduced pressure and the residue purified via silica gel flash chromatography using EtOAc/hexane (1:12, v/v) to afford the title compound as a viscous oil (348 mg, 77%). 1H NMR (400 MHz, CDCl3) δ 1.40 (s, 9H), 2.03 (s, 3H), 3.99 (s, 4H), 6.10 (s, 1H), 6.88 (m, 4H), 7.07 (m, 1H), 7.10-7.27 (m, 10H), 7.38 (d, 1H), 7.47 (t, 1H), 7.71 (s, 1H), 7.77 (d, 1H). ES-MS m/z 565.4 (MH)+; HPLC RT (min) 4.37.

後処理

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe solid residue removed by filtration
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified via silica gel flash chromatography

出典と根拠

ORDレコード
ord-da19d40e49494f96896c0c92dc16087a
出典データセット
uspto-grants-2007_09
特許番号
US07265144B2

関連ノート

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