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

HRID 2217772

反応式

HRID 2217772 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 713105441,1'-Bis(di-tert-butylphosphino)ferrocene触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
130 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-3a2c616e16f14c24b8bb67d401799729
出典データセット
uspto-grants-2008_08
特許番号
US07408076B2

関連ノート

読み込み中…