Potassium Phosphate, Tribasic → HCID 24826750, compound

HRID 911008Notes

Reaction equation

HRID 911008 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[Cl:8][C:9]1[CH:14]=[C:13]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].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>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]>[ClH:8].[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][N:17]=3)[CH:12]=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 63778831HCID 63778831, compound

Product 1

HCID 24826750HCID 24826750, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (0.477 g, 4.18 mmol), 2-chloro-4-(pyridin-2-ylthio)pyridine (0.930 g, 4.18 mmol), potassium phosphate (0.975 g, 4.59 mmol), Pd2(dba)3 (0.191 g, 0.209 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.121 g, 0.209 mmol) were reacted to provide 4-methyl-N-(4-(pyridin-2-ylthio)pyridin-2-yl)thiazol-2-amine hydrochloride (0.310 g, 44% yield). 1H NMR (d6-DMSO) δ 11.55 (bs, 1H), 8.62 (d, 1H), 8.31 (d, 1H), 7.89 (t, 1H), 7.59 (d, 1H), 7.44 (m, 1H), 7.36 (s, 1H), 7.08 (d, 1H), 6.83 (s, 1H), 2.31 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-df1e51e24ff940fca270719976671c85
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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