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

HRID 1743481

反応式

HRID 1743481 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
66 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-b9d5409cc1b7456b83176fa1d2dc298e
出典データセット
uspto-grants-2006_03
特許番号
US07008636B2

関連ノート

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