Tetrahydrofuran → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine

HRID 1177396ノート

反応式

HRID 1177396 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17](Cl)[N:16]=3)=[C:9]([F:23])[CH:8]=1.C1COCC1.[Br-].[CH2:30]([Zn+])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>[NH4+].[Cl-].CCOC(C)=O.[Pd](Cl)Cl.C(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C.C(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:16]=3)=[C:9]([F:23])[CH:8]=1

参加物

7

反応物 3

HCID 8028TetrahydrofuranHCID 591748622-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridineHCID 178419772HCID 178419772、化合物

生成物 1

HCID 591748722-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine

試薬・触媒・溶媒 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
70 °C

実験手順

A thick slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine (2.50 g, 7.1 mmol) and bis(4-(di-tert-butylphosphino)-N,N-dimethyl-benzenamine) palladium dichloride (0.10 g, 0.14 mmol) in benzylzinc(II) bromide 0.5M in THF (21 mL, 11 mmol) was flushed with argon and sealed, and heated to 70° C. All solids eventually dissolved over 1 h to give a dark brown solution. After 3 h, the reaction mixture was cooled and diluted with sat'd aq. NH4Cl. Solid formed, and was taken up in EtOAc. The organic layer was washed sat'd aq. NH4Cl, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting solid was suspended in 50 mL MTBE and stirred for 30 min, then filtered, rinsing with a minimum amount of MTBE, and dried in vacuo to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine as a gray solid. MS (ESI) m/z: Calculated: 406.1; Observed: 407.1 (M++1).

後処理

  1. customsealed
  2. dissolutionAll solids eventually dissolved over 1 h
  3. customto give a dark brown solution
  4. temperaturethe reaction mixture was cooled
  5. customSolid formed
  6. washThe organic layer was washed
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. filtrationfiltered
  11. washrinsing with a minimum amount of MTBE
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-e11f90b96e974b0a9ecec6b56a7d01e8
出典データセット
uspto-grants-2010_11
特許番号
US07842685B2

反応ノート

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