Potassium Phosphate, Tribasic → HCID 24826581, compound

HRID 910979Notes

Reaction equation

HRID 910979 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[CH3:22])[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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:11]2[CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[CH:14]=[CH:9][N:10]=2)[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 63778674HCID 63778674, compound

Product 1

HCID 24826581HCID 24826581, compoundYield 50.2%

Reagents, catalysts & solvents 2

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

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (0.291 g, 2.55 mmol), 2-chloro-4-(o-tolylthio)pyridine (0.600 g, 2.55 mmol), potassium phosphate (0.595 g, 2.80 mmol), Pd2(dba)3 (0.117 g, 0.127 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.074 g, 0.127 mmol) were reacted to provide 4-methyl-N-(4-(o-tolylthio)pyridin-2-yl)thiazol-2-amine (0.401 g, 50% yield). 1H NMR (d6-DMSO) δ 11.04 (s, 1H), 8.07 (d, 1H), 7.57 (d, 1H), 7.47 (d, 2H), 7.34 (m, 1H), 6.63 (s, 1H), 6.50 (s, 1H), 6.48 (m, 1H), 2.34 (s, 3H), 2.19 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-49030423f681414292e692cbf02f848a
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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