Tetrahydrofuran → HCID 90118085, compound

HRID 523159Notes

Reaction equation

HRID 523159 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH:3]=1.CC1(C)C(C)(C)OB([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1COCC1>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CCOC(C)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:5]=[C:4]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH:3]=1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 27606054,4,5,5-Tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolaneHCID 901181032-(4,6-Dichloropyridin-2-yl)thiazole

Product 1

HCID 90118085HCID 90118085, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 2 dram vial equipped with a stir bar was added 2-(4,6-dichloropyridin-2-yl)thiazole (50 mg, 0.22 mmol), 4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (59 mg, 0.22 mmol), Pd(dppf)Cl2 (8 mg, 11 μmol) and K3PO4 (344 mg, 1.62 mmol). The vial was capped with a septum screwcap and then placed under N2 atmosphere. To the vial was added THF (1 mL) and water (0.5 mL). The mixture was placed in a 60° C. heating block with stirring for 16 h. The reaction mixture was cooled to room temperatured; diluted with MeOH and then concentrated in vacuo. The resulting residue was dissolved/suspended in CH2Cl2 and then filtered through Celite. The filtrate was concentrated to afford a solid orange residue. This material was subjected to silica gel chromatography (hexanes:EtOAc, 100:0 to 95:5) to afford 2-(4-chloro-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)thiazole as a white solid (46 mg, 62%). 1H-NMR (400 MHz, CDCl3) 8.23 (d, J=1.8 Hz, 2H), 8.21 (s, 1H), 7.98 (d, J=3.3 Hz, 1H), 7.80 (d, J=1.5 Hz, 2H), 7.78 (s, 1H), 7.53 (d, J=3.3 Hz, 1H).

Workup

  1. customTo a 2 dram vial equipped with a stir bar
  2. customThe vial was capped with a septum screwcap
  3. customwas placed in a 60° C.
  4. temperatureheating block
  5. temperatureThe reaction mixture was cooled to room
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered through Celite
  8. concentrationThe filtrate was concentrated
  9. customto afford a solid orange residue

Sources & evidence

ORD record
ord-f235e764f19b41608afe7c356397c3a7
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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