Potassium Carbonate → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine

HRID 1177391Notes

Reaction equation

HRID 1177391 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([C:13](B(O)O)=[CH2:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:18]1[CH2:23][CH2:22][CH2:21][O:20][CH:19]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[S:31][C:32]3[C:37]([N:38]=2)=[CH:36][CH:35]=[C:34](Cl)[N:33]=3)=[C:26]([F:40])[CH:25]=1>O1CCOCC1.O.C(Cl)Cl.CC(=O)OCC.[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:20]1[CH2:21][CH2:22][CH2:23][O:18][CH:19]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[S:31][C:32]3[C:37]([N:38]=2)=[CH:36][CH:35]=[C:34]([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH2:14])[N:33]=3)=[C:26]([F:40])[CH:25]=1

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 5003684(1-Phenylvinyl)boronic acidHCID 591748622-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine

Product 1

HCID 671118192-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 5

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of bis(4-(di-tert-butylphosphino)-N,N-dimethylbenzenamine) palladium dichloride (0.252 g, 0.356 mmol), potassium carbonate (6.70 g, 48.5 mmol), 1-phenylvinylboronic acid (4.64 g, 31.4 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine (5.00 g, 14.3 mmol) in 50 mL dioxane and 15 mL water was sealed and heated to 80° C. overnight. The reaction was cooled, diluted with DCM, water, and the aq. Layer was extracted with DCM. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown semi-solid. The solid was suspended in 100 mL EA, heated to 75° C., and filtered, rinsing with a small volume of hot EA. The filtrate was allowed to stand overnight, resulting in crystals, and was placed in the freezer overnight. The resulting crystals were collected by filtration, rinsing with a small volume of cold EA to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)-thiazolo[5,4-b]pyridine as light brown crystals. MS (ESI) m/z: Calculated: 418.1; Observed: 419.0 (M++1).

Workup

  1. customwas sealed
  2. temperatureThe reaction was cooled
  3. extractionthe aq. Layer was extracted with DCM
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown semi-solid
  8. temperatureheated to 75° C.
  9. filtrationfiltered
  10. washrinsing with a small volume of hot EA
  11. customresulting in crystals
  12. customwas placed in the freezer overnight
  13. filtrationThe resulting crystals were collected by filtration
  14. washrinsing with a small volume of cold EA

Sources & evidence

ORD record
ord-aadaa573b03540ffb86b9a0ab1ddae8f
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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