Potassium Phosphate, Tribasic → HCID 24826584, compound

HRID 910983Notes

Reaction equation

HRID 910983 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[C:22]([F:25])([F:24])[F:23])[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:9]2[CH:14]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:23])[F:24])[CH:12]=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634732HCID 86634732, compound

Product 1

HCID 24826584HCID 24826584, compoundYield 75%

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 (0.236 g, 2.07 mmol), 2-chloro-4-(2-(trifluoromethyl)phenylthio)pyridine (0.600 g, 2.07 mmol), potassium phosphate (0.484 g, 2.28 mmol), Pd2(dba)3 (0.095 g, 0.104 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.060 g, 0.104 mmol) were reacted to provide 4-methyl-N-(4-(2-(trifluoromethyl)phenylthio)pyridin-2-yl)thiazol-2-amine (0.568 g, 75% yield). 1H NMR (d6-DMSO) δ 11.06 (s, 1H), 8.10 (d, 1H), 7.99 (d, 1H), 7.76-7.83 (m, 3H), 6.66 (s, 1H), 6.59 (m, 1H), 6.52 (s, 1H), 2.19 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1efd639270b64ef282703d54b3a51f4c
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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