N-methylpropyn-2-ylamine → 4-(3-Methylamino-1-propinyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21216

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.[CH3:42][NH:43][CH2:44][C:45]#[CH:46]>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>[CH3:42][NH:43][CH2:44][C:45]#[C:46][C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[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]

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 (80.0 mg, 0.135 mmol) was dissolved in diethylamine (4.0 mL), and the solution was treated with bis(triphenylphosphine)dichloropalladium (14.3 mg, 0.203 mmol), copper iodide (11.6 mg, 0.0608 mmol) and N-methylpropargylamine (0.114 mL, 1.35 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=5/1 to 3/1) to obtain 4-(3-methylamino-1-propinyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (32.6 mg, yield 47%).

後処理

customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=5/1 to 3/1)

出典と根拠

ORDレコード: ord-b4566a3487594e7a89a222e96db8ab23
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

関連ノート