Sodium Carbonate → HCID 19921681, 화합물

HRID 1463340노트

반응식

HRID 1463340 반응식
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1I.[CH3:14][C:15]([Si:18]([CH3:30])([CH3:29])[O:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:17][C:15]([Si:18]([CH3:29])([CH3:30])[O:19][CH2:20][CH2:21][CH2:22][C:23]1[C:3]2[C:2](=[CH:12][CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=2)[NH:1][C:24]=1[Si:25]([CH3:26])([CH3:27])[CH3:28])([CH3:14])[CH3:16]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 459320Ethyl 4-amino-3-iodobenzoateHCID 10923628HCID 10923628, 화합물

생성물 1

HCID 19921681HCID 19921681, 화합물수율 65%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of ethyl 4-amino-3-iodobenzoate {Hirschfeld et al. J. Med Chem. 1992, 35, 2231-2238.} (7.80 g, 26.8 mmol), [5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentynyl]tri methylsilane (9.41 g, 34.8 mmol), tetra-n-butylammonium chloride (7.44 g, 26.8 mmol), sodium carbonate (14.20 g, .134 mol), triphenylphosphine (0.35 g, 1.3 mmol), and palladium (II) acetate (0.30 g, 1.3 mmol) in 200 mL of DMF, was heated at 98° C. under N2 for 2 h. The solution was cooled, and the bulk of the DMF was removed in vacuo. The mixture was diluted with ethyl acetate, and the organic solution was washed with aqueous NaHCO3, dried (brine, MgSO4), filtered, and concentrated in vacuo. Silica gel chromatography (10:1 hexanes-EtOAc) of the concentrate yielded the title compound (7.49 g, 65%) as a crystalline solid. Recrystallization from hexanes provided an analytical sample as a white crystalline solid: mp 115°-116° C. Anal. Calcd for C23H39N1O3Si2 : C 63.69; H, 9.06; N, 3.23. Found: C, 63.54; H, 9.11; N, 3.17.

후처리

  1. temperatureThe solution was cooled
  2. customthe bulk of the DMF was removed in vacuo
  3. additionThe mixture was diluted with ethyl acetate
  4. washthe organic solution was washed with aqueous NaHCO3
  5. dry with materialdried (brine, MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9751c2fb32444fedb2c1fd347956805d
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05300506

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