Potassium Phosphate, Tribasic → N-(4-(2,6-dichlorophenylthio)pyridin-2-yl)-4-isopropylthiazol-2-amine

HRID 910991Notes

Reaction equation

HRID 910991 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([NH2:9])[S:7][CH:8]=1)([CH3:3])[CH3:2].Cl[C:11]1[CH:16]=[C:15]([S:17][C:18]2[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:25])[CH:14]=[CH:13][N:12]=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>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]>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[S:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([NH:9][C:6]2[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 70640774-(Propan-2-yl)-1,3-thiazol-2-amineHCID 866347352-Chloro-4-(2,6-dichlorophenylthio)pyridine

Product 1

HCID 24826660N-(4-(2,6-dichlorophenylthio)pyridin-2-yl)-4-isopropylthiazol-2-amineYield 38.1%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using the method of Example 3, Step B, 4-isopropylthiazol-2-amine (0.245 g, 1.72 mmol), 2-chloro-4-(2,6-dichlorophenylthio)pyridine (0.500 g, 1.72 mmol), potassium phosphate (0.402 g, 1.89 mmol), Pd2(dba)3 (0.079 g, 0.086 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.050 g, 0.086 mmol) were reacted to provide N-(4-(2,6-dichlorophenylthio)pyridin-2-yl)-4-isopropylthiazol-2-amine (0.260 g, 38% yield) as a white powder. 1H NMR (d6-DMSO) δ 11.07 (s, 1H), 8.10 (d, 1H), 7.76 (d, 2H), 7.64 (t, 1H), 6.57 (s, 1H), 6.56 (d, 1H), 6.51 (s, 1H), 2.82 (hextet, 1H), 1.18 (d, 6H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6202ecd980154e6aa79ccf6b1a7fb7e5
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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