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

HRID 21209

反応式

HRID 21209 の反応式
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:42](=[O:45])([O-])[O-].[K+].[K+].O>C(COC)OC>[OH:45][C:42]1[CH:14]=[CH:15][C:7]([C:7]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[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:8][CH:9]=1

参加物

5

反応物 3

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

生成物 1

HCID 684910644-(4-Hydroxyphenyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone収率 131.9%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

In a similar manner to Step 1 of Example 152, 4-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (300 mg, 0.505 mmol) was dissolved in dimethoxyethane (21 mL), and the solution was treated with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenol (222 mg, 1.01 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (33.0 mg, 0.0404 mmol), potassium carbonate (349 mg, 2.53 mmol) and water (0.182 mL), followed by purification by flash column chromatography (chloroform/methanol=90/10 to 80/20) to obtain 4-(4-hydroxyphenyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (179 mg, yield 66%).

後処理

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=90/10 to 80/20)

出典と根拠

ORDレコード
ord-31afba6c7a0d4894af8378ad3dca1ed1
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

関連ノート

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