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Water → N-[2-cyclopropyl-7-(1,5-dimethyl-6-oxopyridin-3-yl)-1-benzofuran-5-yl]ethanesulfonamide

HRID 518577
ノート
印刷プレビュー

反応式

HRID 518577 の反応式
[CH:1]1([C:4]2[O:5][C:6]3[C:12](I)=[CH:11][C:10]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:9][C:7]=3[CH:8]=2)[CH2:3][CH2:2]1.[CH3:20][N:21]1[CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=[C:23]([CH3:36])[C:22]1=[O:37].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:1]1([C:4]2[O:5][C:6]3[C:12]([C:25]4[CH:24]=[C:23]([CH3:36])[C:22](=[O:37])[N:21]([CH3:20])[CH:26]=4)=[CH:11][C:10]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:9][C:7]=3[CH:8]=2)[CH2:3][CH2:2]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

7

反応物 4

HCID 962Water2 回HCID 11430Potassium CarbonateHCID 712703091,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-oneHCID 118022204N-(2-cyclopropyl-7-iodo-1-benzofuran-5-yl)ethanesulfonamide

生成物 1

HCID 118021844N-[2-cyclopropyl-7-(1,5-dimethyl-6-oxopyridin-3-yl)-1-benzofuran-5-yl]ethanesulfonamide収率 47%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of the title compound from Step 3 (500 mg, 1.3 mmol) and 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (380 mg, 1.5 mmol) in 10 mL of DMF was added K2CO3 (50 mg, 3.8 mmol), water (2 mL) and Pd(dppf)Cl2 (30 mg) under N2. The reaction mixture was heated to 100° C. for 1 h. The resulting mixture was poured into 100 mL of water and extracted with DCM (100 mL×2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with EtOAc to give the title compound (230 mg, 47% yield) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.81 (d, J=3.6 Hz, 1H), 7.67-7.66 (m, 1H), 7.26 (t, J=1.2 Hz, 1H), 7.12 (d, J=3.2 Hz, 1H), 6.54 (br, 1H), 6.36 (d, J=0.8 Hz, 1H), 3.67 (s, 3H), 3.14-3.06 (m, 2H), 2.25 (s, 3H), 2.11-2.00 (m, 1H), 1.38-1.43 (m, 3H), 1.09-0.92 (m, 4H). LCMS: 387 (M+1)+.

後処理

  1. extractionextracted with DCM (100 mL×2)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with EtOAc

出典と根拠

ORDレコード
ord-cd0376b772cf481ab21eb1d7f180b670
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115114B2

反応ノート

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