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

HRID 1177396노트

반응식

HRID 1177396 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e11f90b96e974b0a9ecec6b56a7d01e8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

반응 노트

불러오는 중…