Potassium Phosphate, Tribasic → N-(4-methylthiazol-2-yl)-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridin-2-amine

HRID 910922Notes

Reaction equation

HRID 910922 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[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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:14]=[C:13]([O:15][CH:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][CH2:17]3)[CH:12]=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 637781082-Chloro-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridine

Product 1

HCID 24825975N-(4-methylthiazol-2-yl)-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridin-2-amineYield 68.33%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (11.59 mL, 4.637 mmol), 2-chloro-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridine (1.095 g, 4.216 mmol), potassium phosphate (0.9844 g, 4.637 mmol), Pd2(dba)3 (0.09651 g, 0.1054 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.06586 g, 0.1138 mmol) were reacted to provide N-(4-methylthiazol-2-yl)-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridin-2-amine (0.972 g, 68.33% yield). 1H NMR (d6-DMSO) δ 10.96 (s, 1H), 8.14 (d, 1H), 7.27 (m, 2H), 7.19 (t, 2H), 6.68 (m, 1H), 6.66 (s, 1H), 6.50 (d, 1H), 5.56 (t, 1H), 2.84 (m, 1H), 2.74 (m, 1H), 2.23 (s, 3H), 2.03 (m, 2H), 1.81 (m, 2H); Mass spectrum (apci) m/z=338.0 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1598efeb7f48440da5f199a65c7531ba
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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