Lithium Chloride → (S)-1-(1-{[2-cyano-4-(1-ethoxyvinyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422539노트

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HRID 2422539 반응식
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([C:8]([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28](Cl)=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([Sn](CCCC)(CCCC)[C:44]([O:46][CH2:47][CH3:48])=[CH2:45])CCC.[Cl-].[Li+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([C:8]([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:44]([O:46][CH2:47][CH3:48])=[CH2:45])=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

7

반응물 3

HCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 66790930(S)-1-{1-[(4-chloro-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

생성물 1

HCID 66791347(S)-1-(1-{[2-cyano-4-(1-ethoxyvinyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a solution of (S)-1-{1-[(4-chloro-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate (900 mg, 1.65 mmol), tributyl (1-ethoxyvinyl)tin (0.6 ml, 1.73 mmol) in dioxane (6 mL) was added lithium chloride (210 mg, 4.96 mmol) and Pd(PPh3)4 (95 mg, 0.083 mmol). The reaction mixture was stirred at 100° C. overnight then cooled to room temperature. The solution was then diluted with ethyl acetate, washed with sat. sol. of ammonium chloride, brine and dried over magnesium sulfate. The crude material was purified on silica gel (eluting solvent: 3% acetone in CH2Cl2) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.52 (s, 1H), 8.42 (d, 2H), 8.39 (d, 1H), 8.30 (d, 2H), 8.05 (d, 1H), 7.95 (s, 1H), 7.75 (dd, 1H), 6.02 (s, 2H), 4.75 (dd, 2H), 4.12 (q, 2H), 3.05 (m, 1H), 2.85 (m, 1H), 1.40 (t, 3H), 1.15 (t, 3H).

후처리

  1. temperaturethen cooled to room temperature
  2. washwashed with sat. sol. of ammonium chloride, brine
  3. dry with materialdried over magnesium sulfate
  4. customThe crude material was purified on silica gel (eluting solvent: 3% acetone in CH2Cl2)

출처 및 근거

ORD 기록
ord-edc1cb95699d428fa2721af814571d51
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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