Water → HCID 24827110, compound

HRID 910898Notes

Reaction equation

HRID 910898 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[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].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>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:23][C:20]2[S:21][CH:22]=[C:18]([CH3:17])[N:19]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 63777944HCID 63777944, compound

Product 1

HCID 24827110HCID 24827110, compoundYield 96.3%

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-(3-methoxyphenoxy)pyridine (2.95 g, 12.5 mmol), 4-methylthiazol-2-amine (28.5 mL, 11.4 mmol), potassium phosphate (2.66 g, 12.5 mmol), Pd2(dba)3 (0.261 g, 0.285 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.181 g, 0.313 mmol) were reacted in toluene (30 mL) and water (8 mL) to provide 4-(3-methoxyphenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (3.44 g, 88.7% yield) as yellow solid. 1H NMR (CDCl3) δ 8.14 (d, 1H), 7.26 (t, 1H), 6.76 (m, 1H), 6.63 (m, 1H), 6.58 (t, 1H), 6.46 (dd, 1H), 6.27 (m, 2H), 3.75 (s, 3H), 2.17 (s, 3H); Mass spectrum (esi) m/z=314 (100) (M+H).

Sources & evidence

ORD record
ord-282390a796a948859aca01c9050fc943
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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