Water → ethyl 5-[4-(2-isopropyloxy-3,5-dimethylpyridin-4-yl)-2-nitrophenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate

HRID 1043953ノート

反応式

HRID 1043953 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C@H:13]3[CH2:17][CH2:16][O:15][CH2:14]3)[N:11]=[CH:10][C:9]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([N+:23]([O-:25])=[O:24])[CH:3]=1.[N+](C1C=C(B2OC(C)(C)C(C)(C)O2)C=CC=1C1N([C@H]2CCOC2)N=CC=1C(OCC)=O)([O-])=O.I[C:60]1[C:65]([CH3:66])=[CH:64][N:63]=[C:62]([O:67][CH:68]([CH3:70])[CH3:69])[C:61]=1[CH3:71].O>CN(C=O)C>[CH:68]([O:67][C:62]1[C:61]([CH3:71])=[C:60]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:12]([C@H:13]4[CH2:17][CH2:16][O:15][CH2:14]4)[N:11]=[CH:10][C:9]=3[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([N+:23]([O-:25])=[O:24])[CH:3]=2)[C:65]([CH3:66])=[CH:64][N:63]=1)([CH3:70])[CH3:69]

参加物

6

反応物 4

HCID 962WaterHCID 866863514-Iodo-2-isopropyloxy-3,5-dimethylpyridineHCID 86686384Ethyl 5-(4-bromo-2-nitrophenyl)-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylateHCID 86686385Ethyl 5-[2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate

生成物 1

HCID 86686383ethyl 5-[4-(2-isopropyloxy-3,5-dimethylpyridin-4-yl)-2-nitrophenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

Ethyl 5-(4-bromo-2-nitrophenyl)-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate obtained in Preparation Example 7-(1) (200 mg) was converted to ethyl 5-[2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate by the same method as in Preparation Example 7-(2). A solution of 4-iodo-2-isopropyloxy-3,5-dimethylpyridine obtained in Preparation Example 47 (142 mg) in DMF (0.5 mL), and water (0.5 mL) were added to the reaction mixture, and the mixture was stirred at 110° C. for two hours. The reaction mixture was cooled to room temperature and then partitioned by adding ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 50% to 100%) to give the title compound (138.1 mg).

後処理

  1. additionwere added to the reaction mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned
  4. additionby adding ethyl acetate and water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 50% to 100%)

出典と根拠

ORDレコード
ord-ced4c1933a0b48baac5ec6d9caa60eae
出典データセット
uspto-grants-2013_10
特許番号
US08563565B2

反応ノート

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