Potassium Phosphate, Tribasic → HCID 24826066, compound

HRID 910934Notes

Reaction equation

HRID 910934 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:17]=[C:18]([CH:23]=[CH:24][CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])[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:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([O:21][CH3:22])=[O:20])[CH:12]=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634721HCID 86634721, compound

Product 1

HCID 24826066HCID 24826066, compoundYield 73.6%

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 (59.5 mL, 23.8 mmol), methyl 3-(2-chloropyridin-4-ylthio)benzoate (6.05 g, 21.6 mmol), potassium phosphate (5.05 g, 23.8 mmol), Pd2(dba)3 (0.495 g, 0.541 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.338 g, 0.584 mmol) were reacted to provide methyl 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)benzoate (5.68 g, 73.5% yield). 1H NMR (d6-DMSO) δ 11.06 (s, 1H), 8.10 (m, 3H), 7.87 (m, 1H), 7.70 (t, 1H), 6.72 (s, 1H), 6.64 (dd, 1H), 6.53 (s, 1H), 3.88 (s, 1H), 2.19 (s, 3H); Mass spectrum (apci) m/z=358.1 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7ca41d4ba2d5462a8ff58936c6982da1
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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