Cesium fluoride → HCID 59840616, compound

HRID 513180Notes

Reaction equation

HRID 513180 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[F:12][C:13]([F:25])([F:24])[O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[F-].[Cs+]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O1CCOCC1>[F:12][C:13]([F:24])([F:25])[O:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 59840616HCID 59840616, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-bromothiazole-4-carboxylate (100 mg, 0.424 mmole), 4-(trifluoromethoxy)phenylboronic acid (113 mg, 0.551 mmole), CsF (129 mg, 0.847 mmole), and bis(tri-t-butylphosphine)palladium(0) (22 mg, 0.043 mmole) were combined in a screw cap vial. To this was added 1,4-dioxane (2 mL). N2 was bubbled through the mixture for 10 seconds. The vial was capped then heated to 100° C. After 6 hr the mixture was cooled to RT, diluted with EtOAc, filtered through a pad of Celite washing with EtOAc, and concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 0-15% EtOAc/hexanes) gave ethyl 2-[4-(trifluoromethoxy)phenyl]-1,3-thiazole-4-carboxylate (71 mg, 53%) as a pale orange solid. 1H NMR (399 MHz, CDCl3): δ 8.18 (s, 1 H); 8.07-8.03 (m, 2 H); 7.30 (d, J=8.4 Hz, 2 H); 4.46 (q, J=7.1 Hz, 2 H); 1.44 (t, J=7.1 Hz, 3 H).

Workup

  1. customcap vial
  2. customN2 was bubbled through the mixture for 10 seconds
  3. customThe vial was capped
  4. temperatureAfter 6 hr the mixture was cooled to RT
  5. additiondiluted with EtOAc
  6. filtrationfiltered through a pad of Celite
  7. washwashing with EtOAc
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3aed09063f7948e587ebe04481a84043
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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