Tetrahydrofuran → HCID 59174872, compound

HRID 1177396Notes

Reaction equation

HRID 1177396 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 59174872HCID 59174872, compound

Reagents, catalysts & solvents 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e11f90b96e974b0a9ecec6b56a7d01e8
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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