Potassium Carbonate → Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

HRID 14002

반응식

HRID 14002 반응식
[CH2:1](B(O)O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+].Br[C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([C:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:26])[CH:24]=1)[C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:28]([N:27]([CH2:31][CH2:32][CH3:33])[C:25]([C:23]1[CH:22]=[C:17]([CH:16]=[C:15]([CH2:1][CH3:2])[CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:26])[CH2:29][CH3:30]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 521157Ethylboronic acidHCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

생성물 1

HCID 22593628Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

Ethylboronic acid (0.800 g, 10.8 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.252 g, 0.360 mmol), potassium carbonate (2.50 g, 18.0 mmol) and lithium chloride (0.151 g, 3.60 mmol) are added to a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (1.23 g, 3.60 mmol) in dry DMF (20 mL). The mixture is heated at 100 degrees C. for 18 hours. The mixture is then partitioned between ethyl acetate and water. The phases are separated and the ethyl acetate phase is washed with saline, dried over sodium sulfate and concentrated. The concentrate is column chromatographed (silica gel; ethyl acetate/hexanes, 15/85) to give the title compound, MS (ESI+) for C17H25NO3 m/z (M+H)+=292.2.

후처리

  1. customThe mixture is then partitioned between ethyl acetate and water
  2. customThe phases are separated
  3. washthe ethyl acetate phase is washed with saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed (silica gel; ethyl acetate/hexanes, 15/85)

출처 및 근거

ORD 기록
ord-87b264a8e2c347b0ba0c3634ea5dddab
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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