2-Aminopyridine → HCID 24826148, compound

HRID 910937Notes

Reaction equation

HRID 910937 reaction equation
N1C=CC=CC=1N.[CH3:8][C:9]1[N:10]=[C:11]([NH2:14])[S:12][CH:13]=1.Cl[C:16]1[CH:21]=[C:20]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[CH:19]=[CH:18][N:17]=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>[CH3:30][O:29][C:25]1[CH:24]=[C:23]([S:22][C:20]2[CH:19]=[CH:18][N:17]=[C:16]([NH:14][C:11]3[S:12][CH:13]=[C:9]([CH3:8])[N:10]=3)[CH:21]=2)[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 63778830HCID 63778830, compound

Product 1

HCID 24826148HCID 24826148, compoundYield 61.7%

Reagents, catalysts & solvents 2

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

Procedure

Preparation of 4-(3-methoxyphenylthio)-N-4-methylthiazol-2-yl)pyridin-2-amine: Using the method of Example 3, Step B, 4-methylthiazol-2-amine (10.8 mL, 4.32 mmol), 2-chloro-4-(3-methoxyphenylthio)pyridine (0.989 g, 3.93 mmol), potassium phosphate (0.917 g, 4.32 mmol), Pd2(dba)3 (0.0899 g, 0.0982 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0625 g, 0.108 mmol) were reacted to provide 4-(3-methoxyphenylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.798 g, 61.7% yield). 1H NMR (d6-DMSO) δ 11.08 (s, 1H), 8.09 (d, 1H), 7.45 (t, 1H), 7.14 (m, 2H), 7.11 (m, 1H), 6.77 (s, 1H), 6.61 (dd, 1H), 6.52 (s, 1H), 3.80 (s, 3H), 2.20 (s, 3H); Mass spectrum (apci) m/z=330.2 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ff45a7747b5d4c71a2070a59d1d64e84
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…