Water → Ethyl 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate

HRID 911029Notes

Reaction equation

HRID 911029 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16](Cl)[CH:15]=1.[CH3:21][C:22]1[N:23]=[C:24]([NH2:27])[S:25][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].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].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:27][C:24]2[S:25][CH:26]=[C:22]([CH3:21])[N:23]=2)[CH:15]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634737Ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoate

Product 1

HCID 24826662Ethyl 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoateYield 89.8%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Following the method of Example 3, Step B, ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoate (1.64 g, 5.26 mmol), 4-methylthiazol-2-amine (0.60 g, 5.26 mmol), potassium phosphate (1.23 g, 5.78 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.241 g, 0.263 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.228 g, 0.394 mmol), water (4 mL) and toluene (13 mL) were combined to give the desired product (1.84 g, 89.8% yield) as a yellow solid.

Sources & evidence

ORD record
ord-017223833aa14b158fd6b4bd5e7ffc58
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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