Cesium carbonate → Methyl 4-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-2-(methylthio)thiazole-5-carboxylate

HRID 1887681Notes

Reaction equation

HRID 1887681 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH2:13][C:14]1[N:15]=[C:16]([S:23][CH3:24])[S:17][C:18]=1[C:19]([O:21][CH3:22])=[O:20].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.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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:1][C:2]1[CH:7]=[C:6]([NH:13][C:14]2[N:15]=[C:16]([S:23][CH3:24])[S:17][C:18]=2[C:19]([O:21][CH3:22])=[O:20])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 609212Methyl 4-amino-2-(methylsulfanyl)-1,3-thiazole-5-carboxylateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27737912-Chloro-4-iodo-5-(trifluoromethyl)pyridine

Product 1

HCID 58155161Methyl 4-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-2-(methylthio)thiazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Method A was applied to a mixture of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (156 mg, 0.51 mmol) and methyl 4-amino-2-(methylthio)thiazole-5-carboxylate (86 mg, 0.42 mmol), Pd2(dba)3 (26 mg, 0.028 mmol), xantphos (21 mg, 0.036 mmol) and cesium carbonate (270 mg, 0.83 mmol) in dioxane (4.5 ml).

Sources & evidence

ORD record
ord-c3afb3c991c04f78a727fb1ac0abdd2b
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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