Water → HCID 24826334, compound

HRID 910952Notes

Reaction equation

HRID 910952 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.Cl[C:9]1[CH:14]=[C:13]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1(C)C=CC=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.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>[Cl:22][C:18]1[CH:17]=[C:16]([S:15][C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH:7][C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)[CH:14]=2)[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 63779018HCID 63779018, compound

Product 1

HCID 24826334HCID 24826334, compoundYield 76.7%

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

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (7.007 mL, 4.905 mmol), 2-chloro-4-(3-chlorophenylthio)pyridine (1.382 g, 5.396 mmol), potassium phosphate (1.145 g, 5.396 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.1123 g, 0.1226 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.07805 g, 0.1349 mmol) were reacted in toluene (7 mL) and water (2 mL) to afford 4-(3-chlorophenylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine (1.256 g, 75.93% yield) as off white solid. 1H NMR (CDCl3) δ 8.11 (d, 1H), 7.51 (t, 1H), 7.38 (m, 2H), 7.30 (m, 1H), 6.58 (dd, 1H), 6.49 (s, 1H), 6.32 (d, 1H), 2.19 (d, 3H); Mass spectrum (esi) m/z=334 (100) (M+H).

Sources & evidence

ORD record
ord-e768481bb0bf45a0a7b3e93f7e26f93b
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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