Sodium Carbonate → HCID 21716630、化合物

HRID 1385994ノート

反応式

HRID 1385994 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:7]=1.[S:13]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](B(O)O)=[CH:24]1)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:10]1[CH:11]=[CH:12][C:8]([C:6]2[CH:7]=[C:2]([C:25]3[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:23]([S:13]([C:16]4[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=4)(=[O:15])=[O:14])[CH:24]=3)[CH:3]=[N:4][CH:5]=2)=[CH:9]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 3857443N-(p-Toluenesulfonyl)indole-3-boronic acidHCID 112764923-Bromo-5-thiophen-3-yl-pyridine

生成物 1

HCID 21716630HCID 21716630、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A deoxygenated solution of 3-bromo-5-thiophen-3-yl-pyridine (250 mg, 1.04 mmol, 1 equiv), 1-tosyl-3-indoleboronic acid (430 mg, 1.36 mmol, 1.31 equiv, prepared according to Zheng, Q; Yang, Y; Martin, A. R. Heterocycles 1994, 37, 1761), Pd(PPh3)4 (60 mg, 0.052 mmol, 0.050 equiv), and 2.0 M Na2CO3 (1.0 mL, 2.0 mmol, 1.9 equiv) in dioxane (10 ml) was heated under argon at reflux for 20 h. The reaction mixture was allowed to cool, then partitioned between water (100 mL) and ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (40% ethyl acetate in hexane) to afford 3-(5-thiophen-3-yl-pyridin-3-yl)-1-(toluene-4-sulfonyl)-indole as a white foam.

後処理

  1. temperatureat reflux for 20 h
  2. temperatureto cool
  3. custompartitioned between water (100 mL) and ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (40% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-941b6e0d85574b52853e53a192d2c720
出典データセット
uspto-grants-2001_07
特許番号
US06265403B1

反応ノート

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