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Cesium carbonate → 5-(11'-fluoro-6'H-spiro[cyclopropane-1,5'-indolo[1,2-h][1,7]naphthyridin]-2'-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595777
ノート
印刷プレビュー

反応式

HRID 595777 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])=[CH:10][C:11]3[O:15][C:14]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)=[C:13]([C:23]([NH:25][CH3:26])=[O:24])[C:12]=3[CH:27]=2)[CH:5]=[CH:4][C:3]=1[C:34]1([CH2:37]O)[CH2:36][CH2:35]1.[F:39][C:40]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:41]=1[CH:42]=[C:43](B1OC(C)(C)C(C)(C)O1)[NH:44]2.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1.O>[F:39][C:40]1[C:41]2[CH:42]=[C:43]3[C:2]4[N:7]=[C:6]([C:8]5[C:9]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:30])=[O:31])=[CH:10][C:11]6[O:15][C:14]([C:16]7[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=7)=[C:13]([C:23]([NH:25][CH3:26])=[O:24])[C:12]=6[CH:27]=5)[CH:5]=[CH:4][C:3]=4[C:34]4([CH2:35][CH2:36]4)[CH2:37][N:44]3[C:45]=2[CH:46]=[CH:47][CH:48]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 532172124-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indoleHCID 903324785-(6-chloro-5-(1-(hydroxymethyl)cyclopropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

生成物 1

HCID 90333908
5-(11'-fluoro-6'H-spiro[cyclopropane-1,5'-indolo[1,2-h][1,7]naphthyridin]-2'-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
収率 5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 5-(6-chloro-5-(1-(hydroxymethyl)cyclopropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (80 mg, 0.143 mmol) and 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (56.1 mg, 0.215 mmol) in 1,4-Dioxane (2 mL) and water (20 μL) was added Cs2CO3 (93 mg, 0.287 mmol) and DTBPF PdCl2 (21 mg, 0.032 mmol). The mixture was heated to 80° C., stirred overnight, concentrated in vacuo and dried. The residue was dissolved in DCM (2.00 mL), followed by addition of triphenylphosphine (94 mg, 0.358 mmol) and DIAD (0.070 mL, 0.358 mmol). The mixture was stirred at RT for 4 h. Preparative TLC (eluted with 20% ethyl acetate in DCM) gave 5-(11′-fluoro-6′H-spiro[cyclopropane-1,5′-indolo[1,2-h][1,7]naphthyridin]-2′-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (4.5 mg, yield: 5%) MS (M+H)+: 639.

後処理

  1. concentrationconcentrated in vacuo
  2. customdried
  3. dissolutionThe residue was dissolved in DCM (2.00 mL)
  4. stirringThe mixture was stirred at RT for 4 h
  5. washPreparative TLC (eluted with 20% ethyl acetate in DCM)

出典と根拠

ORDレコード
ord-d550062794c14c15ae004fd05eedff87
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09243002B2

反応ノート

読み込み中…

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