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Ethyl Acetate → HCID 117771658、化合物

HRID 2201530
ノート
印刷プレビュー

反応式

HRID 2201530 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:22][C:23]3[CH:33]=[C:32]([N:34]([CH3:39])[S:35]([CH3:38])(=[O:37])=[O:36])[C:31](B4OC(C)(C)C(C)(C)O4)=[CH:30][C:24]=3[C:25]=2[C:26]([NH:28][CH3:29])=[O:27])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>O1CCOCC1.O.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]>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:22][C:23]3[CH:33]=[C:32]([N:34]([CH3:39])[S:35]([CH3:38])(=[O:36])=[O:37])[C:31]([C:2]4[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH3:13])=[CH:4][CH:3]=4)=[CH:30][C:24]=3[C:25]=2[C:26](=[O:27])[NH:28][CH3:29])=[CH:17][CH:16]=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 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 682394022-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamideHCID 70700803Methyl 6-bromo-3-methoxypicolinate

生成物 1

HCID 117771658HCID 117771658、化合物収率 91.2%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
60 °C

実験手順

To a stirring mixture of methyl 6-bromo-3-methoxypicolinate (200 mg, 0.81 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (408 mg, 0.81 mmol) and K2CO3 (146 mg, 1.06 mmol) in dioxane/H2O (4 mL/0.2 mL) was added Pd(dppf)Cl2 (20 mg) under N2 protection. The mixture was stirred at 60° C. for 5 h, and after concentrated in vacuo, the residue was extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography (PE:EtOAc=2:1, then 1:1) to give the product of methyl 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-methoxypicolinate (400 mg, yield: 90%). 1H-NMR (CDCl3, 400 MHz) δ 7.88˜7.92 (m, 3H), 7.70 (d, J=8.8 Hz, 1H), 7.56 (s, 1H), 7.40 (d, J=8.8 Hz, 1H), 7.14 (t, J=8.8 Hz, 2H), 5.85 (d, J=3.2 Hz, 1H), 3.91 (s, 3H), 3.89 (s, 3H), 3.15 (s, 3H), 2.92 (d, J=4.8 Hz, 3H), 2.72 (s, 3H). MS (M+H)+: 542.

後処理

  1. concentrationafter concentrated in vacuo
  2. extractionthe residue was extracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography (PE

出典と根拠

ORDレコード
ord-61c259ec66b44a70bd76ba625767a9b8
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09364482B2

反応ノート

読み込み中…

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