Potassium Phosphate, Tribasic → HCID 24826254, compound

HRID 910950Notes

Reaction equation

HRID 910950 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]=[CH:18][C:17]=2[Cl:22])[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:14]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 63778493HCID 63778493, compound

Product 1

HCID 24826254HCID 24826254, compoundYield 83.6%

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 (7.88 mL, 5.52 mmol), 2-chloro-4-(2-chlorophenylthio)pyridine (1.55 g, 6.07 mmol), potassium phosphate (1.29 g, 6.07 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.126 g, 0.138 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0878 g, 0.152 mmol) were reacted in toluene (8 mL) to afford 4-(2-chlorophenylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine (1.54 g, 82.8% yield) as yellow solid. 1H NMR (CDCl3) δ 8.11 (d, 1H), 7.59 (dd, 1H), 7.53 (dd, 1H), 7.38 (dt, 1H), 7.29 (dt, 1H), 6.56 (dd, 1H), 6.48 (d, 1H), 2.23 (s, 3H); Mass spectrum (esi) m/z 334 (100) (M+H).

Sources & evidence

ORD record
ord-8b13becc7b6a40889abac8787c42e778
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…