Water → HCID 24827108, compound

HRID 910894Notes

Reaction equation

HRID 910894 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]1[N:21]=[C:22]([NH2:25])[S:23][CH:24]=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>[CH3:19][C:20]1[N:21]=[C:22]([NH:25][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=3)[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][N:3]=2)[S:23][CH:24]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634715HCID 86634715, compound

Product 1

HCID 24827108HCID 24827108, compoundYield 73.9%

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

Methyl 3-(2-chloropyridin-4-yloxy)benzoate (3.05 g, 11.6 mmol), 4-methylthiazol-2-amine (26.3 mL, 10.5 mmol), potassium phosphate (2.45 g, 11.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.241 g, 0.263 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.167 g, 0.289 mmol) were reacted in toluene (26 mL) and water (8 mL) according to Example 17, Step B to afford methyl 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate (2.65 g, 68.7% yield) as yellow solid. 1H NMR (CDCl3) δ 8.15 (d, J=5.85 Hz, 1H), 7.89 (dt, J=1.17, 7.80 Hz, 1H), 7.70 (m, 1H), 7.45 (t, J=7.80 Hz, 1H), 7.24 (m, 1H), 6.44 (dd, J=1.95, 5.85 Hz, 1H), 6.25 (m, 2H), 3.88 (s, 3H), 2.14 (d, J=1.17 Hz, 3H). Mass spectrum (esi) m/z=342 (100) (M+H).

Sources & evidence

ORD record
ord-77b2363b5e614b918013bf61899094e1
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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