Toluene → HCID 57898928, compound

HRID 911027Notes

Reaction equation

HRID 911027 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]([O:17][C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])[CH:14]=[CH:13][N:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O.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:1]([C:4]1[N:5]=[C:6]([NH:9][C:11]2[CH:16]=[C:15]([O:17][C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([O:23][CH3:24])=[O:22])[CH:14]=[CH:13][N:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 70640774-(Propan-2-yl)-1,3-thiazol-2-amineHCID 86634715HCID 86634715, compound

Product 1

HCID 57898928HCID 57898928, compoundYield 83.2%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

Following the method of Example 1, Step B, 4-isopropylthiazol-2-amine (10.55 mL, 4.219 mmol), methyl 3-(2-chloropyridin-4-yloxy)benzoate (1.224 g, 4.641 mmol), potassium phosphate (0.9850 g, 4.641 mmol), tris(dibenzylideneacetone)dipalladium (0). (0.09658 g, 0.1055 mmol), and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.06713 g, 0.1160 mmol) were reacted in water (3 mL) and toluene (11 mL) to give the title compound (1.297 g, 81.55% yield) as yellow solid. 1H NMR (CDCl3) δ 8.19 (d, 1H), 7.93 (dt, 1H), 7.76 (m, 1H), 7.50 (t, 1H), 7.30 (m, 1H), 6.50 (m, 1H), 6.48 (dd, 1H), 6.33 (s, 1H), 3.92 (s, 3H), 2.87 (m, 1H), 1.22 (d, 6H).

Sources & evidence

ORD record
ord-2448528f436f4870b50aefca4fc9e3fc
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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