Triethylamine → 5-(1-Benzenesulfonyl-7-fluoroindol-3-yl)-thiophene-2-carboxaldehyde

HRID 644072ノート

反応式

HRID 644072 の反応式
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[F:19])[C:12](Br)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([C:23]1[S:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].C(N(CC)CC)C>C(O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[F:19])[C:12]([C:26]3[S:27][C:23]([CH:21]=[O:22])=[CH:24][CH:25]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 27734305-Formyl-2-thiopheneboronic acidHCID 596035291-benzenesulfonyl-3-bromo-7-fluoro-1H-indole

生成物 1

HCID 860732925-(1-Benzenesulfonyl-7-fluoroindol-3-yl)-thiophene-2-carboxaldehyde収率 77.3%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 1-benzenesulfonyl-3-bromo-7-fluoroindole (0.5 g, 1.41 mmol), 5-formyl-2-thiophene boronic acid (0.24 g, 1.55 mmol), bis(triphenylphosphine) palladium (II) dichloride (0.06 g, 0.08 mmol) and triethylamine (0.39 ml, 2.82 mmol) in ethanol (4 ml) was subjected to microwave irradiation at 150° C. for 420 s. The resulting suspension was concentrated under reduced pressure and the residue passed through a silica pad eluting with dichloromethane to afford crude 5-(1-benzenesulfonyl-7-fluoroindol-3-yl)-thiophene-2-carboxaldehyde as a brown solid (0.42 g) which was used in the next step with no further purification.

後処理

  1. customirradiation at 150° C. for 420 s
  2. concentrationThe resulting suspension was concentrated under reduced pressure
  3. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-095010febf2f47b587cb51c8dfe3d52b
出典データセット
uspto-grants-2010_04
特許番号
US07700634B2

反応ノート

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