Cesium carbonate → 5'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one

HRID 472998노트

반응식

HRID 472998 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3([CH2:15][CH2:14][C:13]4[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=4[CH2:11][CH2:10]3)[C:7](=[O:20])[C:6]=2[CH:21]=1.[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([F:29])[CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:22][C:23]1[CH:24]=[C:25]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]4([CH2:10][CH2:11][C:12]5[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=5[CH2:14][CH2:15]4)[C:7](=[O:20])[C:6]=3[CH:21]=2)[CH:26]=[C:27]([F:29])[CH:28]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 15391287(3-Chloro-5-fluorophenyl)boronic acidHCID 581970305'-bromo-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one

생성물 1

HCID 581980625'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one수율 92.5%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
110 °C

실험 절차

A 10 mL microwave tube was charged with 5′-bromo-5,6,8,9-tetrahydro-3′H-spiro[benzo[7]annulene-7,2′-benzofuran]-3′-one (0.0573 g, 0.167 mmol), 3-chloro-5-fluorophenylboronic acid (0.0930 g, 0.53 mmol), Cs2CO3 (0.2537 g, 0.78 mmol), 1,4-dioxane (4 mL), water (1 mL), and PdCl2(PPh3)2 (0.0118 g, 0.0168 mmol). The tube was heated in a CEM microwave reactor at 110° C. for 30 min. The reaction mixture was diluted with CH2Cl2 and dried over Na2SO4. After the solvent was evaporated under reduced pressure, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.0607 g (92%) of 5′-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3′H-spiro[benzo[7]annulene-7,2′-benzofuran]-3′-one. LC-MS tR=2.55 min in 3 min chromatography, m/z 393, 395 (MH+).

후처리

  1. dry with materialdried over Na2SO4
  2. customAfter the solvent was evaporated under reduced pressure
  3. customthe residue was purified by chromatography on silica gel
  4. washeluted with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-c5f8b9d8c4a44e2e9effa3dc696bcc63
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633212B2

반응 노트

불러오는 중…