Potassium Carbonate → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylvinyl)benzo[d]thiazole

HRID 1177442Notes

Reaction equation

HRID 1177442 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[CH:38]=[C:37](Br)[CH:36]=[CH:35][C:33]=3[N:34]=2)=[C:26]([F:40])[CH:25]=1>O1CCOCC1.CO>[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[CH:38]=[C:37]([C:13]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[CH2:14])[CH:36]=[CH:35][C:33]=3[N:34]=2)=[C:26]([F:40])[CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5003684(1-Phenylvinyl)boronic acidHCID 671120772-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole

Product 1

HCID 671116092-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylvinyl)benzo[d]thiazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A slurry of (amphos)2PdCl2 (0.114 g, 0.161 mmol), potassium carbonate (2.85 g, 20.6 mmol), 1-phenylvinylboronic acid (2.10 g, 14.2 mmol), 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole (2.54 g, 6.44 mmol) in 20 mL dioxane/4 mL water was flushed with argon and sealed, and heated at 90° C. overnight. In the morning the reaction mixture was cooled and judged complete by LCMS. The reaction mixture was partitioned between EA/H2O and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to give a solid. The material was suspended in MeOH, and filtered. The resulting solid was dried in vacuo to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylvinyl)benzo[d]thiazole as a dull yellow solid. MS (ESI) m/z: Calculated: 417.1; Observed: 418.0 (M++1).

Workup

  1. customsealed
  2. temperatureIn the morning the reaction mixture was cooled
  3. customThe reaction mixture was partitioned between EA/H2O
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a solid
  9. filtrationfiltered
  10. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-afaf6320f00c43f7b6138894d25f8be9
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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