Water → HCID 24825976, compound

HRID 910924Notes

Reaction equation

HRID 910924 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.Cl[C:9]1[CH:19]=[C:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=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>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:9]2[CH:19]=[C:18]([O:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634720HCID 86634720, compound

Product 1

HCID 24825976HCID 24825976, compoundYield 80.6%

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, 4-methylthiazol-2-amine (25.2 mL, 10.1 mmol), ethyl 6-chloro-4-(naphthalen-1-yloxy)nicotinate (3.63 g, 11.1 mmol), potassium phosphate (2.35 g, 11.1 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.231 g, 0.252 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.160 g, 0.277 mmol) were reacted in toluene (25 mL) and water (8 mL) to afford ethyl 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinate (3.30 g, 80.0% yield) as yellow solid. 1H NMR (CDCl3) δ 9.90 (bs, 1H), 8.91 (s, 1H), 7.97 (d, 1H), 7.91 (d, 1H), 7.77 (d, 1H), 7.53 (m, 1H), 7.47 (m, 1H), 7.43 (m, 1H), 7.14 (d, 1H), 6.18 (s, 1H), 5.90 (s, 1H), 4.37 (quart, 2H), 1.76 (s, 3H), 1.33 (t, 3H); Mass spectrum (apci) m/z=406 (100) (M+H).

Sources & evidence

ORD record
ord-75cd6cf08dd84fac860f92fd318cfcda
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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