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

HRID 1527163

反応式

HRID 1527163 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c12580fb42b24572b9f6d64137f543fa
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

関連ノート

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