Diisopropylethylamine → tert-Butyl {3-[(2-morpholin-4-yl-5-nitrophenyl)ethynyl]phenyl}carbamate

HRID 541954

반응식

HRID 541954 반응식
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[C:17]([C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=[CH:23][CH:24]=1)#[CH:18].C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=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>[N:11]1([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[C:18]#[C:17][C:19]2[CH:20]=[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH:22]=[CH:23][CH:24]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 27658874-(2-Bromo-4-nitrophenyl)morpholineHCID 11275982tert-Butyl 3-ethynylphenylcarbamate

생성물 1

HCID 57962728tert-Butyl {3-[(2-morpholin-4-yl-5-nitrophenyl)ethynyl]phenyl}carbamate수율 70%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A solution of 4-(2-bromo-4-nitrophenyl)morpholine (0.27 g, 0.95 mmol), tert-butyl (3-ethynylphenyl)carbamate, and bis(triphenylphosphine)palladium(II) chloride (67 mg, 95 μmol) in N,N-dimethylformamide (4.4 mL) was treated with N,N-diisopropylethylamine (0.21 mL, 1.2 mmol) and stirred at 80° C. for 16 h. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to give a crude residue. This material was purified by flash column chromatography to give the desired product (0.28 g, 70%) as a solid. LCMS for C23H26N3O5 (M+H)+: m/z=424.0.

후처리

  1. washwashed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a crude residue
  6. customThis material was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-7108b44f371d48c2bcf50b01928421d7
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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