Water → HCID 24825873, compound

HRID 910908Notes

Reaction equation

HRID 910908 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.Cl[C:9]1[CH:14]=[C:13]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:12]=[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].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH:16]1([O:15][C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH:7][C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)[CH:14]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 63777039HCID 63777039, compound

Product 1

HCID 24825873HCID 24825873, compoundYield 31.3%

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 (3.50 mL, 1.40 mmol), 2-chloro-4-(cyclohexyloxy)pyridine (0.326 g, 1.54 mmol), potassium phosphate (0.327 g, 1.54 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.0321 g, 0.0350 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.0223 g, 0.0385 mmol) were reacted in toluene (4 mL) and water (1.5 mL) to afford N-(4-(cyclohexyloxy)pyridin-2-yl)-4-methylthiazol-2-amine (0.127 g, 30.7% yield) as white solid. 1H NMR (CDCl3) δ 8.12 (d, 1H), 6.43 (d, 1H), 6.35 (bs, 1H), 6.32 (d, 1H), 4.29 (m, 1H), 2.34 (d, 3H), 1.97 (m, 2H), 1.80 (m, 2H), 1.54 (m, 3H), 1.36 (m, 3H); Mass spectrum (apci) m/z=290 (100) (M+H).

Sources & evidence

ORD record
ord-8b61dfa456a94d089d832df55d8482d0
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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