Indole → (E)-1-(2-([1,1'-Biphenyl]-4-yloxy)vinyl)-1H-indole

HRID 1053507

반응식

HRID 1053507 반응식
I/[CH:2]=[CH:3]/[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I>[C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]([O:4]/[CH:3]=[CH:2]/[N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 798IndoleHCID 10796Cesium carbonateHCID 89873752(E)-4-((2-Iodovinyl)oxy)-1,1'-biphenyl

생성물 1

HCID 89873720(E)-1-(2-([1,1'-Biphenyl]-4-yloxy)vinyl)-1H-indole수율 87%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

실험 절차

The compound 9 was prepared following the procedure described for 5 with 4 (0.32 g, 1 mmol, 1 eq), indole (0.14 g, 1.2 mmol, 1.2 eq), Cs2CO3 (0.81 g, 2.5 mmol, 2.5 eq), CuI (0.095 g, 0.5 mmol, 0.5 eq) and L2 (0.097 g, 0.5 mmol, 0.5 eq) at 70° C. for 12 h to give crude product which were purified by silica gel column chromatography using ethyl acetate-hexane (9:95) to afford compound 9 as white crystals (0.27 g, 87%): mp 140-142° C. 1H NMR (300 MHz, CDCl3): 7.58-7.46 (m, 6H, HAr), 7.40-7.32 (m, 3H, HAr), 7.25-7.21 (m, 1H, HAr), 7.20-7.14 (m, 2H, HAr), 7.12-7.02 (m, 4H, HAr and H(O)C═(N)CH), 6.55 (d, H, J=3.1 Hz, HAr). 13C NMR (75 MHz, CDCl3): 156.8, 140.4, 136.5, 136.4, 128.9, 128.8, 128.5, 127.1, 126.9, 125.7, 125.6, 121.2, 120.5, 116.5, 115.2, 109.8, 104.0 ppm; IR (cm−1): 3034, 2358, 2338, 1682, 1606, 1515, 1485, 1475, 1462, 1358, 1333, 1322, 1301, 1232, 1202, 1186, 1174, 1134, 1115, 1088, 1031, 1007, 907, 865, 834; HRMS (ESI), Calculated for C22H17NO [M+H]+ 312.1388. Found 312.1381; Elemental analysis Calculated for C22H17NO.0.25H2O: C, 83.65; H, 5.58; N, 4.43. found: C, 83.61; H, 5.65; N, 4.01.

후처리

  1. customThe compound 9 was prepared
  2. customto give crude product which
  3. customwere purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a07f4b7584ae45d89e0479383454e1fe
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09393306B2

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