Potassium Phosphate, Tribasic → HCID 24827112, compound

HRID 910902Notes

Reaction equation

HRID 910902 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+].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.O.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]>[CH3:15][C:16]1[N:17]=[C:18]([NH:21][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[S:19][CH:20]=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 117889672-Chloro-4-phenoxypyridine

Product 1

HCID 24827112HCID 24827112, compoundYield 23.6%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 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) in toluene (8 mL) and water (2 mL) afforded N-(4-methylthiazol-2-yl)-4-phenoxypyridin-2-amine (170 mg, 23% yield) as yellow solid. 1H NMR (CDCl3) δ 9.72 (bs, 1H), 8.17 (d, 1H), 7.41 (m, 2H), 7.25 (m, 1H), 7.08 (m, 2H), 6.48 (dd, 1H), 6.30 (s, 1H), 6.28 (d, 1H), 2.19 (d, 3H); Mass spectrum (esi) m/z=284 (100) (M+H).

Sources & evidence

ORD record
ord-ed48c183921543b0a26ac1830a0b2c7a
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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