Sodium Acetate → HCID 68782473, compound

HRID 2266456Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22]S(C(F)(F)F)(=O)=O)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:7]2[CH3:21].C([Si]([O:37][C:38]([O:40][CH3:41])=[CH2:39])(C)C)(C)(C)C.C([O-])(=O)C.[Na+]>CN(C)C=O.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:41][O:40][C:38](=[O:37])[CH2:39][O:22][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[C:7]([CH3:21])=[C:8]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:9]([CH3:12])=[N:10]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of trifluoromethanesulfonic acid 8-chloro-3-(4-chlorophenoxy)-2,4-dimethylquinolin-5-yl ester (0.20 g), tert-butyl-(1-methoxyvinyloxy)dimethyl silane (0.40 g), sodium acetate (0.044 g), tris(dibenzylideneacetone) dipalladium (0.020 g) and 1,1′-bis(diphenylphospino) ferrocene (0)(0.012 g) in N,N-dimethylformamide (5.0 mL) was heated by microwave irradiation at 120° C. for 15 minutes. The mixture was purified by column chromatography on silica gel, eluting with a mixture of pentane and dichloromethane (9:1 to 0:1 by volume) to afford title compound as a yellow oil, 0.034 g.

Workup

customThe mixture was purified by column chromatography on silica gel
washeluting with a mixture of pentane and dichloromethane (9:1 to 0:1 by volume)

Sources & evidence

ORD record: ord-22d8216e2e554beea83283546c8a7436
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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