Water → t-Butyl 2-(4-amino-2-fluoro-phenyl)-pyrrole-1-carboxylate

HRID 13353

반응식

HRID 13353 반응식
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][C:25]=1[F:31]>C(COC)OC>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:9]2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=[CH:11][CH:10]=2)=[C:25]([F:31])[CH:26]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 8218484-Bromo-3-fluoroanilineHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

생성물 1

HCID 23145615t-Butyl 2-(4-amino-2-fluoro-phenyl)-pyrrole-1-carboxylate

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
70 °C

실험 절차

1.6 g of 1-(t-butoxycarbonyl)pyrrole-2-boronic acid, 200 mg of tetrakistriphenylphosphine palladium, 5 ml of aqueous saturated sodium carbonate solution and 5 ml of water were added in order to a dimethoxyethane (10 ml) solution of 1 g of 4-bromo-3-fluoro-phenylamine, and the reaction liquid was stirred in a nitrogen atmosphere at 70° C. for 3 hours. After cooled, the reaction liquid was filtered through Celite, and the filtrate was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1) to obtain the entitled compound as a pale brown solid.

후처리

  1. customthe reaction liquid
  2. temperatureAfter cooled
  3. customthe reaction liquid
  4. filtrationwas filtered through Celite
  5. additionthe filtrate was diluted with ethyl acetate
  6. washwashed with water and saturated saline in order
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe solvent was evaporated away under reduced pressure
  9. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-c32cc0a9d4634d88a4893cadde34f050
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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