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

HRID 644072노트

반응식

HRID 644072 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-095010febf2f47b587cb51c8dfe3d52b
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700634B2

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