Propargyl alcohol → 4-(3-Hydroxy-1-propynyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21215

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.[CH2:42]([OH:45])[C:43]#[CH:44]>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[OH:45][CH2:42][C:43]#[C:44][C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:39]

参加物

実験手順

In a similar manner to Step 2 of Example 161, 4-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (60.0 mg, 0.101 mmol) was dissolved in diethylamine (3.0 mL), and the solution was treated with bis(triphenylphosphine)dichloropalladium (8.6 mg, 0.012 mmol), copper iodide (6.9 mg, 0.036 mmol), propargyl alcohol (0.029 mL, 0.51 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=5/1) to obtain 4-(3-hydroxy-1-propinyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (18.8 mg, yield 37%).

後処理

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

出典と根拠

ORDレコード: ord-ce138090a4a54cb38cae9b163b2fc22c
出典データセット: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07745641B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 3

実験手順

後処理

出典と根拠

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