Cesium carbonate → HCID 58958594, 화합물

HRID 915602

반응식

HRID 915602 반응식
[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

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 7706433-tert-Butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine2회HCID 3731394N,N-dibenzyl-2-bromobenzenesulfonamide

생성물 1

HCID 58958594HCID 58958594, 화합물수율 77%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da19d40e49494f96896c0c92dc16087a
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265144B2

연결된 노트

불러오는 중…