Potassium Phosphate, Tribasic → HCID 24826507, compound

HRID 910975Notes

Reaction equation

HRID 910975 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][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])[CH:12]=[CH:11][N:10]=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]>[F:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:16]=1[O:15][C:13]1[CH:14]=[CH:9][N:10]=[C:11]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86634728HCID 86634728, compound

Product 1

HCID 24826507HCID 24826507, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (0.284 g, 2.48 mmol), 2-chloro-4-(2,6-difluorophenoxy)pyridine (0.600 g, 2.48 mmol), potassium phosphate (0.580 g, 2.73 mmol), Pd2(dba)3 (0.114 g, 0.124 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.072 g, 0.124 mmol) were reacted to provide N-(4-(2,6-difluorophenoxy)pyridin-2-yl)-4-methylthiazol-2-amine (0.312 g, 39% yield). 1H NMR (d6-DMSO) δ 11.03 (s, 1H), 8.20 (d, 1H), 7.36-7.50 (m, 3H), 6.60-6.63 (m, 2H), 6.54 (s, 1H), 2.20 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-3e6f7fbc8cc94f20b2f65150b1f54201
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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