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2,4-Difluoro-1-iodobenzene → 6-amino-5-bromo-2-(2,4-difluorophenyl)-N-methylbenzofuran-3-carboxamide

HRID 595653
ノート
印刷プレビュー

反応式

HRID 595653 の反応式
[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12](=[O:15])[NH:13][CH3:14])=[C:7](B(O)O)[O:8][C:4]=2[CH:3]=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1I>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]>[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12]([NH:13][CH3:14])=[O:15])=[C:7]([C:23]3[CH:22]=[CH:21][C:20]([F:19])=[CH:25][C:24]=3[F:26])[O:8][C:4]=2[CH:3]=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

5

反応物 2

HCID 1375192,4-Difluoro-1-iodobenzeneHCID 90332513(6-Amino-5-bromo-3-(methylcarbamoyl)benzofuran-2-yl)boronic acid

生成物 1

HCID 903324766-amino-5-bromo-2-(2,4-difluorophenyl)-N-methylbenzofuran-3-carboxamide収率 70.5%

試薬・触媒・溶媒 2

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

反応条件

温度
15 °C

実験手順

To a mixture of (6-amino-5-bromo-3-(methylcarbamoyl)benzofuran-2-yl)boronic acid (4.78 g, 11.46 mmol), K3PO4.3H2O (8.32 g, 31.25 mmol) and 2,4-difluoro-1-iodobenzene (2.50 g, 10.42 mmol) in DMF (25 mL) was added Pd(dppf)Cl2 (380 mg, 0.52 mmol) under N2, and then the mixture was stirred at 15° C. for 3 hours. After the solvent was removed, EtOAc/H2O (10 mL/20 mL) was added to the mixture. After stirring 15 minutes, the resulting solid was filtered to give the product of 6-amino-5-bromo-2-(2,4-difluorophenyl)-N-methylbenzofuran-3-carboxamide (2.80 g, yield: 70%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.06 (d, J=1.6 Hz, 1H), 7.74 (d, J=10.4 Hz, 1H), 7.70 (s, 1H), 7.41 (s, 1H), 7.24 (s, 1H), 7.00 (s, 1H), 5.58 (br s, 2H), 2.76 (s, 3H). MS (M+H)+: 281/283

後処理

  1. customAfter the solvent was removed
  2. additionEtOAc/H2O (10 mL/20 mL) was added to the mixture
  3. stirringAfter stirring 15 minutes
  4. filtrationthe resulting solid was filtered

出典と根拠

ORDレコード
ord-95cb501410ad4f28881291adcb92963a
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

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