Cesium carbonate → 6-Vinyl-1H-indole-3-carbaldehyde

HRID 1527163노트

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HRID 1527163 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH:13]([B-](F)(F)F)=[CH2:14].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>Cl[Pd]Cl.O.C1COCC1>[CH:13]([C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1)=[CH2:14]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 27948306-Bromoindole-3-carbaldehydeHCID 23679353Potassium vinyltrifluoroborate

생성물 1

HCID 866737896-Vinyl-1H-indole-3-carbaldehyde

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

6-bromoindole-3-carboxaldehyde (5 g, 22.3 mmol), potassium vinyltrifluoroborate (4.48 g, 33.5 mmol), PdCl2 (396 mg, 2.23 mmol), PPh3 (1.75 mg, 6.7 mmol) and Cs2CO3 (2.18 mg, 66.9 mmol) were combined in a 500 mL flask placed under a nitrogen atmosphere. THF (135 mL) and H2O (15 mL) were added and the yellow solution was heated at 85° C. for 2 days. The reaction was allowed to cool to RT, water was added and the mixture was extracted twice with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1) to give the title compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.4; MS (LC/MS): 172.0 [M+H]+ 170.1 [M−H]−; tR (HPLC conditions a): 2.95 min.

후처리

  1. temperatureto cool to RT
  2. extractionthe mixture was extracted twice with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1)

출처 및 근거

ORD 기록
ord-c12580fb42b24572b9f6d64137f543fa
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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