Water → HCID 24827111, compound

HRID 910900Notes

Reaction equation

HRID 910900 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:17][C:18]1[N:19]=[C:20]([NH2:23])[S:21][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1(C)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].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:23][C:20]3[S:21][CH:22]=[C:18]([CH3:17])[N:19]=3)[CH:7]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 11253330HCID 11253330, compound

Product 1

HCID 24827111HCID 24827111, compoundYield 48.4%

Reagents, catalysts & solvents 3

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

Procedure

Using the method of Example 3, Step B, 2-chloro-4-(4-methoxyphenoxy)pyridine (2.952 g, 12.53 mmol), 4-methylthiazol-2-amine (28.47 mL, 11.39 mmol), potassium phosphate (2.417 g, 11.39 mmol), Pd2(dba)3, (0.2607 g, 0.2847 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.1812 g, 0.3131 mmol) were reacted in toluene (30 mL) and water (8 mL) to provide 4-(4-methoxyphenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (1.726 g, 44.50% yield) as yellow solid. 1H NMR (CDCl3) δ 8.10 (d, 1H), 6.96 (m, 2H), 6.87 (m, 2H), 6.42 (dd, 1H), 6.26 (d, 1H), 6.18 (d, 1H), 3.80 (s, 3H), 2.15 (s, 3H); Mass spectrum (esi) m/z=314 (100) (+H).

Sources & evidence

ORD record
ord-4669f15c391b4e0fb913c648e91bc065
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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