Potassium Phosphate, Tribasic → HCID 66803800, compound

HRID 2366264Notes

Reaction equation

HRID 2366264 reaction equation
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([F: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])([CH3:23])([CH3:22])[CH3:21].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.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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]>[C:20]([O:24][C:25](=[O:27])[NH:26][C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([F: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)([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86669007HCID 86669007, compound

Product 1

HCID 66803800HCID 66803800, compoundYield 72.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-bromo-2-(2-chloro-6-fluorophenyl)-7-fluorothiazolo[5,4-c]pyridine (0.440 g, 1.22 mmol), carbamic acid tert-butyl ester (0.714 g, 6.1 mmol), XantPhos (0.071 g, 0.122 mmol) and K3PO4 (0.530 g, 2.5 mmol) in toluene (8 mL) and water (1.2 mL) was degassed with a stream of argon. Pd2(dba)3 (0.056 g, 0.061 mmol) was added and the reaction mixture was heated in a sealed vial at 70° C. for 3 hours. After cooling to room temperature, the crude mixture was filtered through Celite® washing with EtOAc. The organic layer was washed with brine, then dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-50% EtOAc in pentane to afford the title compound as a white solid (350 mg, 72% yield). LCMS (Method D): RT=4.08 min, m/z: 398 [M+H+].

Workup

  1. customwas degassed with a stream of argon
  2. temperatureAfter cooling to room temperature
  3. filtrationthe crude mixture was filtered through Celite®
  4. washwashing with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified by column chromatography on silica gel eluting with 0-50% EtOAc in pentane

Sources & evidence

ORD record
ord-c9854d20e7b8417597db50b6975f6864
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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