Water → HCID 24825874, compound

HRID 910910Notes

Reaction equation

HRID 910910 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][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>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:9]2[CH:14]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 11401777HCID 11401777, compound

Product 1

HCID 24825874HCID 24825874, compoundYield 70.6%

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 (3.50 mL, 1.40 mmol), 2-chloro-4-(phenylthio)pyridine (0.342 g, 1.54 mmol), potassium phosphate (0.327 g, 1.54 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.0321 g, 0.0350 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0223 g, 0.0385 mmol) were reacted in toluene (4 mL) and water (1.5 mL) to afford 4-methyl-N-(4-(phenylthio)pyridin-2-yl)thiazol-2-amine (0.296 g, 69.8% yield) as off white solid. 1H NMR (CDCl3) δ 8.07 (d, 1H), 7.54 (m, 2H), 7.44 (m, 3H), 6.57 (dd, 1H), 6.45 (d, 1H), 6.32 (d, 1H), 2.24 (d, 3H); Mass spectrum (apci) m/z=300 (100) (M+H).

Sources & evidence

ORD record
ord-36e9b7fea4a8471298691950645e33f0
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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