Potassium Phosphate, Tribasic → Ethyl 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate

HRID 910995Notes

Reaction equation

HRID 910995 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[Cl:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23](Cl)[CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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>[Cl:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[O:20][C:21]1[CH:22]=[CH:23][N:24]=[C:25]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:26]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634737Ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoate

Product 1

HCID 24826662Ethyl 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoateYield 56.2%

Reagents, catalysts & solvents 2

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

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (0.329 g, 2.88 mmol), ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoate (0.900 g, 2.88 mmol), potassium phosphate (0.673 g, 3.17 mmol), Pd2(dba)3 (0.132 g, 0.144 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.083 g, 0.144 mmol) were reacted to provide ethyl 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate (0.631 g, 56% yield). 1H NMR (d6-DMSO) δ 10.99 (s, 1H), 8.20 (d, 1H), 7.92 (d, 1H), 7.83-7.87 (m, 2H), 6.51-6.57 (m, 3H), 4.32 (quartet, 2H), 2.20 (s, 3H), 1.31 (t, 2H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a215fd06262a4cc385efc382ebc51dc1
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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