Potassium Phosphate, Tribasic → HCID 66801353, compound

HRID 2366273Notes

Reaction equation

HRID 2366273 reaction equation
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[C:5]([F:19])=[CH:4][N:3]=1.[C:20]([O:24][C:25](=[O:27])[NH2:26])(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:20][O:24][C:25](=[O:27])[NH:26][C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[C:5]([F:19])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 86669011HCID 86669011, compound

Product 1

HCID 66801353HCID 66801353, compoundYield 124.3%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of 4-bromo-2-(2,6-dichlorophenyl)-7-fluorothiazolo[5,4-c]pyridine (0.60 g, 1.6 mmol), carbamic acid tert-butyl ester (0.936 g, 8.0 mmol), XantPhos (0.093 g, 0.16 mmol) and K3PO4 (0.678 g, 3.2 mmol), in toluene (10 mL) and water (2 mL), was degassed with a stream of argon. Pd2(dba)3 (0.073 g, 0.08 mmol) was added and the reaction mixture was heated at 70° C. for 3 hours in a sealed vial. After cooling to room temperature, the crude reaction mixture was filtered through Celite® washing with EtOAc. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-40% EtOAc in pentane to afford the title compound as an off-white/yellow solid (0.74 g). LCMS (Method D): RT=4.26 min, m/z: 414 [M+H+].

Workup

  1. customin toluene (10 mL) and water (2 mL), was degassed with a stream of argon
  2. temperatureAfter cooling to room temperature
  3. customthe crude reaction mixture
  4. filtrationwas filtered through Celite®
  5. washwashing with EtOAc
  6. extractionThe aqueous phase was further extracted with EtOAc
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe resultant residue was purified by column chromatography on silica gel eluting with 0-40% EtOAc in pentane

Sources & evidence

ORD record
ord-fe01d721f28646ac9b24a2deef1a7872
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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