Potassium Carbonate → HCID 86685281, 화합물

HRID 402844

반응식

HRID 402844 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:14]=[O:15])=[CH:5][N:6]2[CH:11]([CH3:13])[CH3:12].[F:16][C:17]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.Cl[Pd]Cl.[Fe]>[CH3:12][CH:11]([N:6]1[C:7]2[C:3](=[C:2]([C:20]3[CH:19]=[CH:18][C:17]([F:16])=[C:22]([F:23])[C:21]=3[F:24])[CH:10]=[CH:9][CH:8]=2)[C:4]([CH:14]=[O:15])=[CH:5]1)[CH3:13]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 772308814-bromo-1-isopropyl-1H-indole-3-carbaldehyde

생성물 1

HCID 86685281HCID 86685281, 화합물수율 68.7%

시약·촉매·용매 3

HCID 178454869HCID 178454869, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
140 °C

실험 절차

To a solution of 4-bromo-1-(propan-2-yl)-1H-indole-3-carboxaldehyde (100 mg, 0.376 mmol) and 2,3,4-trifluorophenylboronic acid (79 mg, 0.451 mmol) in dioxane (2 mL) and water (0.5 mL) in a 5 mL microwave reaction vial was added potassium carbonate (156 mg, 1.13 mmol) and dichloro[1,1′-bis(di-t-butylphosphino)ferrocene]palladium (II) (25 mg, 0.038 mmol). The reaction was placed under nitrogen, sealed and heated in a microwave reactor at 140° C. for 15 minutes. The solvent was removed in vacuo and the residue was partitioned with ethyl acetate and aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (COMBI FLASH 24 gm column, gradient of 0-100% ethyl acetate/hexanes) to give the title intermediate (82 mg).

후처리

  1. customsealed
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned with ethyl acetate and aqueous sodium bicarbonate
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel (COMBI FLASH 24 gm column, gradient of 0-100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-32e07e7475ba49d9b3530fab92a58071
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

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