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Dichloromethane → 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid methyl ester

HRID 1915057
ノート
印刷プレビュー

反応式

HRID 1915057 の反応式
Br[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[F:22])=[O:13])[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:34]2[NH:38][CH:37]=[C:36]([C:39]([O-:41])=[O:40])[CH:35]=2)O1.[CH2:43](Cl)Cl>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]>[CH3:43][O:41][C:39]([C:36]1[CH:35]=[C:34]([C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:25]=[CH:24][CH:23]=[C:11]([C:12](=[O:13])[NH:14][C:15]4[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=4[F:22])[CH:10]=3)[CH:5]=[CH:4][N:3]=2)[NH:38][CH:37]=1)=[O:40]
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 3

HCID 6344DichloromethaneHCID 581678683-(2-bromo-pyridin-4-yloxy)-N-(2-fluoro-5-methyl-phenyl)-benzamideHCID 866515565-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-3-carboxylate

生成物 1

HCID 510016275-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid methyl ester収率 2,806.2%

試薬・触媒・溶媒 1

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

反応条件

温度
95 °C

実験手順

A mixture of 3-(2-bromo-pyridin-4-yloxy)-N-(2-fluoro-5-methyl-phenyl)-benzamide (200 mg, 0.50 mmol), methyl-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-3-carboxylate (251 mg, 1.0 mmol) and PdCl2(dppf).CH2Cl2 (10 mg, 0.012 mmol) was added to a thick-walled reaction vessel and purged with N2. A solution of 2M Na2CO3 (0.5 mL) was added, followed by DMSO (8 mL). The reaction vessel was sealed and the mixture stirred at 95° C. for 16 h. The reaction vessel was cooled to room temperature and the mixture was poured into 100 ml of water. The precipitates were filtered, washed with water and dried to give the crude, which was purified via column chromatography eluting with 30-40% EtOAc/hexanes to afford 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid methyl ester (150 mg, 58% yield).

後処理

  1. custompurged with N2
  2. additionA solution of 2M Na2CO3 (0.5 mL) was added
  3. customThe reaction vessel was sealed
  4. temperatureThe reaction vessel was cooled to room temperature
  5. additionthe mixture was poured into 100 ml of water
  6. filtrationThe precipitates were filtered
  7. washwashed with water
  8. customdried
  9. customto give the crude, which
  10. customwas purified via column chromatography
  11. washeluting with 30-40% EtOAc/hexanes

出典と根拠

ORDレコード
ord-e58b778c0e234f7c825e1100a0846665
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08614234B2

反応ノート

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