(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-thiazolo[5,4-b]pyridin-5-yl)(cyclobutyl)methanone → 1-(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)-1-cyclobutyl-2-(trimethylsilyl)ethanol

HRID 1177590

反応式

HRID 1177590 の反応式
[CH3:1][Si:2]([CH2:5][Mg]Cl)([CH3:4])[CH3:3].[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[C:27]([N:28]=2)=[CH:26][CH:25]=[C:24]([C:29]([CH:31]2[CH2:34][CH2:33][CH2:32]2)=[O:30])[N:23]=3)=[C:16]([F:35])[CH:15]=1>C1COCC1>[O:10]1[CH2:11][CH2:12][CH2:13][O:8][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[C:27]([N:28]=2)=[CH:26][CH:25]=[C:24]([C:29]([CH:31]2[CH2:32][CH2:33][CH2:34]2)([OH:30])[CH2:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[N:23]=3)=[C:16]([F:35])[CH:15]=1

参加物

4

反応物 2

HCID 67112767(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-thiazolo[5,4-b]pyridin-5-yl)(cyclobutyl)methanoneHCID 178418680HCID 178418680、化合物

生成物 1

HCID 671116841-(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)-1-cyclobutyl-2-(trimethylsilyl)ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

Trimethylsilylmethylmagnesium chloride (1.1M solution in THF; 1.12 mL, 1.23 mmol) was added to a solution of (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)(cyclobutyl)methanone (327.0 mg, 0.821 mmol) in THF (15 mL) at 25° C., and the resulting solution was stirred at 25° C. for 5 min. Excess Grignard reagent was quenched by the careful addition of sat. aq. NH4Cl (5 mL), water was added to dissolve precipitated salts, and THF was then removed in vacuo. The resulting solution was partitioned between EtOAc (100 mL) and sat. aq. NH4Cl (20 mL), and the organic layer was separated and washed with brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to provide 1-(2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)-1-cyclobutyl-2-(trimethylsilyl)ethanol as a yellow oil. MS (ESI) m/z: Calculated: 486.2; Observed: 487.1 (M++1).

後処理

  1. customExcess Grignard reagent was quenched by the careful addition of sat. aq. NH4Cl (5 mL), water
  2. additionwas added
  3. dissolutionto dissolve
  4. customprecipitated salts, and THF
  5. customwas then removed in vacuo
  6. customThe resulting solution was partitioned between EtOAc (100 mL) and sat. aq. NH4Cl (20 mL)
  7. customthe organic layer was separated
  8. washwashed with brine
  9. dry with materialThe organic layer was then dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-641d1d88f7ce45769389047ef7c18ee2
出典データセット
uspto-grants-2010_11
特許番号
US07842685B2

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