Potassium Phosphate, Tribasic → HCID 24827114, compound

HRID 910906Notes

Reaction equation

HRID 910906 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])[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+].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>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].O>[CH3:19][C:20]1[N:21]=[C:22]([NH:25][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:4][N:3]=2)[S:23][CH:24]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86634716HCID 86634716, compound

Product 1

HCID 24827114HCID 24827114, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Using the method of Example 3, Step B, methyl 2-(2-chloropyridin-4-yloxy)benzoate (1.91 g, 7.23 mmol), 4-methylthiazol-2-amine (16.4 mL, 6.57 mmol), potassium phosphate (1.53 g, 7.23 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.105 g, 0.181 mmol) and Pd2(dba)3 (0.150 g, 0.164 mmol) were reacted in toluene (16 mL) and water (5 mL) to provide methyl 2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate as yellow solid. 1H NMR (CDCl3) δ 8.16 (d, 1H), 8.01 (dd, 1H), 7.57 (m, 1H), 7.35 (dt, 1H), 7.13 (d, 1H), 6.43 (dd, 1H), 6.29 (d, 1H), 6.21 (dc, 1H), 3.75 (s, 3H), 2.19 (d, 3H); Mass spectrum (esi) m/z=342 (100) (M+H).

Sources & evidence

ORD record
ord-2914521748ff4a8ea9af93e64cf9c49d
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…