Potassium Phosphate, Tribasic → HCID 86634739, compound

HRID 910999Notes

Reaction equation

HRID 910999 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:12][C:13]1[S:14][CH:15]=[C:16]([CH3:18])[N:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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>[CH3:18][C:16]1[N:17]=[C:13]([NH:12][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[S:14][CH:15]=1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 2736842Methyl 2-chloropyridine-4-carboxylate

Product 1

HCID 86634739HCID 86634739, compoundYield 71.5%

Reagents, catalysts & solvents 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Using the method of Example 3, Step B, 2-chloroisonicotinic acid, methyl ester (4.734 g, 27.59 mmol), 2-amino-4-methylthiazole (3.0 g, 26.28 mmol), potassium phosphate (2.393 ml, 28.90 mmol), Pd2(dba)3 (0.6016 g, 0.6569 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.4181 g, 0.7226 mmol) in toluene (20 mL) and water (0.5 mL) were reacted to afford methyl 2-(4-methylthiazol-2-ylamino)isonicotinate (4.682 g, 71.48% yield) as a white solid. 1H NMR (CDCl3) δ 10.25 (bs, 1H), 8.47 (dd, 1H), 7.40 (m, 1H), 7.39 (dd, 1H), 6.45 (d, 1H), 3.94 (s, 3H), 2.39 (d, 3H); Mass spectrum (apci) m/z=250 (100) (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2b61e565dc9a4270a140a1bbde9c7167
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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