Water → 4-(4-Aminophenyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21207

반응식

HRID 21207 반응식
FC(F)(F)S(O[C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:39])(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:7]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[C:18]4[C:23]([CH:24]=3)=[CH:22][C:21]([CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:20][CH:19]=4)=[C:12]3[C:8]=2[CH2:9][NH:10][C:11]3=[O:39])=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 866282864-Trifluoromethanesulfonyloxy-7-(1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

생성물 1

HCID 684907404-(4-Aminophenyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone수율 114%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

In a similar manner to Step 1 of Example 152, 4-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (150 mg, 0.250 mmol) was dissolved in dimethoxyethane (10.5 mL), and the solution was treated with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)aniline (110 mg, 0.500 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (25 mg, 0.030 mmol), potassium carbonate (173 mg, 1.25 mmol) and water (0.090 mL), followed by purification by preparative thin-layer chromatography (chloroform/methanol=5/1) to obtain 4-(4-aminophenyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (76.5 mg, yield 57%).

후처리

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=5/1)

출처 및 근거

ORD 기록
ord-adbe54d81ace4ddea6c63b31e3211520
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

연결된 노트

불러오는 중…