Sodium Chloride → HCID 69001310, compound

HRID 2044202Notes

Reaction equation

[CH3:1][N:2]([CH3:26])[C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([C:20]([F:23])([F:22])[F:21])[C:14]=1[F:24].[CH:27]([Sn](CCCC)(CCCC)CCCC)=[CH2:28].CCOC(C)=O.[Na+].[Cl-]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]([CH3:26])[C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:27]=[CH2:28])=[C:15]([C:20]([F:23])([F:22])[F:21])[C:14]=1[F:24]

Participants

Conditions

Temperature: 120 °C

Procedure

5-Methyl-2-(2′-fluoro-4′-bromo-3′-trifluoromethylanilino)phenylacetic acid N,N-dimethyl amide prepared by method outlined in example 3 (0.8 g, 1.7 mmol), Pd(PPh3)4 (0.1 g, 0.09 mmol), and vinyl tributylstannane (0.6 g, 1.9 mmol) in DMF (5 mL) is heated to 120° C. under nitrogen overnight. After cooling, the reaction is portioned between EtOAc and saturated aqueous solution of NaCl. The separated organic layer is washed twice with fresh saturated aqueous solution of NaCl. The EtOAc layer is dried and concentrated under reduced pressure. The residue is purified by flash chromatography to give 5-Methyl-2-(2′-fluoro-4′-vinyl-3′-trifluoromethylanilino)phenylacetic acid N,N-dimethyl amide.

Workup

temperatureAfter cooling
washThe separated organic layer is washed twice with fresh saturated aqueous solution of NaCl
dry with materialThe EtOAc layer is dried
concentrationconcentrated under reduced pressure
customThe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-465fab2ef4934bff863ab91a6f3ab623
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586782B2

Reaction notes

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