Water → HCID 24827113, compound

HRID 910904Notes

Reaction equation

HRID 910904 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:15][C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=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>[CH3:15][C:16]1[N:17]=[C:18]([NH:21][C:2]2[CH:7]=[C:6]([O:8][C:9]3[C:14]4[C:13](=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:12]=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[S:19][CH:20]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 117889672-Chloro-4-phenoxypyridine

Product 1

HCID 24827113HCID 24827113, compoundYield 79.8%

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-phenoxypyridine (0.575 g, 2.79 mmol), 4-methylthiazol-2-amine (6.35 mL, 2.54 mmol), potassium phosphate (0.593 g, 2.79 mmol), Pd2(dba)3 (0.0582 g, 0.0635 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0404 g, 0.0699 mmol) were reacted in toluene (6 mL) and water (2 mL) to provide N-(4-methylthiazol-2-yl)-4-(naphthalen-1-yloxy)pyridin-2-amine (0.371 g, 77.8% yield) as off white solid. 1H NMR (CDCl3) δ 8.13 (d, 1H), 7.90 (m, 2H), 7.76 (d, 1H), 7.53 (m, 1H), 7.46 (m, 2H), 7.18 (d, 1H), 6.49 (dd, 1H), 6.25 (m, 2H), 2.09 (s, 3H); Mass spectrum (esi) m/z=334 (100) (N+H).

Sources & evidence

ORD record
ord-00010667543946dc879cc5861c8b1bdd
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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