Potassium Phosphate, Tribasic → HCID 24826753, compound

HRID 911011Notes

Reaction equation

HRID 911011 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])[CH:5]=[C:4]([Cl:17])[N:3]=1.[CH3:18][C:19]1[N:20]=[C:21]([NH2:24])[S:22][CH:23]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>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]>[Cl:17][C:4]1[N:3]=[C:2]([NH:24][C:21]2[S:22][CH:23]=[C:19]([CH3:18])[N:20]=2)[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])[CH:5]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86634744HCID 86634744, compound

Product 1

HCID 24826753HCID 24826753, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,6-dichloro-4-(2,6-difluorophenoxy)pyridine (552 mg, 2.0 mmol), 4-methylthiazol-2-amine (228 mg, 2.0 mmol), potassium phosphate (466 mg, 2.20 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.092 g, 0.100 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.167 g, 0.100 mmol) in degassed toluene (5 mL) and water (2 mL) is heated at 90° C. for 12 hours and then cooled to room temperature. The reaction mixture is partitioned between water and ethyl acetate to afford N-(6-chloro-4-(2,6-difluorophenoxy)pyridin-2-yl)-4-methylthiazol-2-amine.

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction mixture is partitioned between water and ethyl acetate

Sources & evidence

ORD record
ord-b5efb411b2e84158933c9db49f8b64d1
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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