Potassium Phosphate, Tribasic → HCID 24826336, compound

HRID 910955Notes

Reaction equation

HRID 910955 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH:5]=[CH:4][N:3]=1.[CH3:17][C:18]1[N:22]=[C:21]([NH2:23])[S:20][N:19]=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>[CH3:17][C:18]1[N:22]=[C:21]([NH:23][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]#[N:12])[CH:5]=[CH:4][N:3]=2)[S:20][N:19]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 3506395-Amino-3-methyl-1,2,4-thiadiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 63777935HCID 63777935, compound

Product 1

HCID 24826336HCID 24826336, compoundYield 2.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Using the method of Example 3, Step B, 2-(2-chloropyridin-4-yloxy)benzonitrile (0.330 g, 1.43 mmol), 3-methyl-1,2,4-thiadiazol-5-amine (3.26 mL, 1.30 mmol), potassium phosphate (0.304 g, 1.43 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.0298 g, 0.0326 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0207 g, 0.0358 mmol) were reacted in toluene (5 mL) and water (1.5 mL) to afford 2-(2-(3-methyl-1,2,4-thiadiazol-5-ylamino)pyridin-4-yloxy)benzonitrile (10 mg) as off white solid. 1H NMR (CDCl3) δ 8.35 (d, 1H), 7.76 (dd, 1H), 7.66 (dt, 1H), 7.37 (dt, 1H), 7.19 (d, 1H), 6.63 (dd, 1H), 6.45 (d, 1H), 2.49 (s, 3H); Mass spectrum (esi) m/z=310 (100) (M+H).

Sources & evidence

ORD record
ord-c64f024e59a74ef198deea7b8fdbab93
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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