Potassium Carbonate → 2-Propyl-3-propyl-5-fluoro-1H-indole

HRID 1246271

반응식

HRID 1246271 반응식
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:9]=1[NH2:10].[CH3:16][CH2:17][CH2:18][C:19]#[C:20][CH2:21][CH2:22][CH3:23]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Fe+2].CN1C(=O)CCC1>[CH2:18]([C:19]1[NH:10][C:9]2[C:8]([C:20]=1[CH2:21][CH2:22][CH3:23])=[CH:14][C:13]([F:15])=[CH:12][CH:11]=2)[CH2:17][CH3:16]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 160294-OctyneHCID 2428732-Bromo-4-fluoroaniline

생성물 1

HCID 219166242-Propyl-3-propyl-5-fluoro-1H-indole수율 80.9%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 713105441,1'-Bis(di-tert-butylphosphino)ferrocene촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
130 °C

실험 절차

A 50 mL three neck flask was charged with palladium acetate (22.4 mg, 0.1 mmol), dtbpf (94 mg, 0.2 mmol), potassium carbonate (690 mg, 5 mmol), 2-bromo-4-fluoroaniline (380 mg, 2 mmol), 4-octyne (264 mg, 2.4 mmol) and NMP (10 ml). The mixture was purged with argon and heated to 130° C. After 1 hr, the reaction mixture was cooled to rt. Ethyl acetate and water were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine and dried with MgSO4. Removal of the solvents and purification of the crude by column chromatography afforded the desired product as yellow oil (355 mg, containing 4.3 wt % AcOEt). The corrected yield was 77.6%.

후처리

  1. customThe mixture was purged with argon
  2. temperaturethe reaction mixture was cooled to rt
  3. additionEthyl acetate and water were added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic phases were washed with water, brine
  7. dry with materialdried with MgSO4
  8. customRemoval of the solvents and purification of the crude by column chromatography

출처 및 근거

ORD 기록
ord-ee56f80cf6cf40bfa928dffb2d2f4444
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07126009B2

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