Dichloromethane → N-(8-indol-1-yl-octyl)-3,5-bis(3-chlorophenyl)4-hydroxybenzamide

HRID 1281426

반응식

HRID 1281426 반응식
[N:1]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:29])[C:20]2[CH:25]=[C:24](I)[C:23]([OH:27])=[C:22](I)[CH:21]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].[Cl:36][C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][CH:42]=1.[CH2:46]([Cl:48])Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[N:1]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:29])[C:20]2[CH:25]=[C:24]([C:41]3[CH:40]=[CH:39][CH:38]=[C:37]([Cl:36])[CH:42]=3)[C:23]([OH:27])=[C:22]([C:3]3[CH:4]=[CH:5][CH:6]=[C:46]([Cl:48])[CH:2]=3)[CH:21]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 22237561N-(8-indol-1-yl-octyl)-3,5-diiodo-4-hydroxybenzamide

생성물 1

HCID 22237625N-(8-indol-1-yl-octyl)-3,5-bis(3-chlorophenyl)4-hydroxybenzamide수율 3,976.5%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
66 °C

실험 절차

A mixture of N-(8-indol-1-yl-octyl)-3,5-diiodo-4-hydroxybenzamide (4.016 g, 6.517 mmol), 2 M K2CO3 (9.8 ml in water), dioxane (100 ml), 3-chlorophenylboronic acid (2.242 g, 14.336 mmol), and [1,1′bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with CH2Cl2 (0.106 g, 0.130 mmol) was warmed to 66° C. After 2 h, the reaction mixture was cooled and concentrated in vac. The residue was taken up in EtOAc (200 ml) and 1N HCl (50 ml). The layers were shaken, separated and the organic layer was washed with 1N HCl (2×50 ml), brine (2×50 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The crude product was purified by flash chromatography (alumina, hexane to 60% EtOAc/Hex gradient) to give a light yellow foam (3.027 g, 79%); 1H NMR (300 MHz, DMSO-d6) δ 1.24 (broad s, 8H), 1.43-1.52 (m, 2H), 1.65-1.75 (m, 2H), 3.16-3.26 (q, J=7.5 Hz, 2H), 4.12 (t, J=7.5 Hz, 2H) 6.38 (d, J=3 Hz, 1H), 6.94-7.00 (m, 1H), 7.05-7.13 (m, 1H), 7.33 (d, J=3 Hz, 1H), 7.40-7.53 (m, 8H), 7.62 (s, 2H), 7.76 (s, 2H), 8.40 (t, J=5 Hz, 1H), 9.19 (s, 1H); mass spectrum [(+)ESI], m/z 585 (M+H)+.

후처리

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated in vac
  3. customseparated
  4. washthe organic layer was washed with 1N HCl (2×50 ml), brine (2×50 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vac
  8. customdried
  9. customThe crude product was purified by flash chromatography (alumina, hexane to 60% EtOAc/Hex gradient)

출처 및 근거

ORD 기록
ord-c843aa3f0f654cedbb88a2033da6f55f
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451827B2

연결된 노트

불러오는 중…