Cesium carbonate → HCID 68996578, compound

HRID 1811541Notes

Reaction equation

[CH3:1][N:2]([CH3:27])[C:3](=[O:26])[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:19]=[CH2:20])=[C:15]([C:21]([F:24])([F:23])[F:22])[C:14]=1[F:25].C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CC(O)C>[CH3:27][N:2]([CH3:1])[C:3](=[O:26])[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]([CH2:19][CH3:20])=[C:15]([C:21]([F:22])([F:23])[F:24])[C:14]=1[F:25]

Participants

Conditions

Temperature: 80 °C

Procedure

The above styrene is reduced under conditions outlined in. The styrene is dissolved in i-PrOH and toluene and degassed for 10 minutes. Then Cs2CO3 (22 mg, 0.07 mmol), [Ir(cod)Cl]2 (44 mg, 0.07 mmol), and dppp (27 mg, 0.07 mmol) are added and the reaction is heated to 80° C. over night. The cooled solution is concentrated in vacuo and the residue purified by flash chromatography eluting with 10, then 20, then 30% EtOAc/hexanes to give the title 5-methyl-2-(2′-fluoro-4′-ethyl-3′-trifluoromethylanilino)phenylacetic acid N,N-dimethyl amide.

Workup

customtoluene and degassed for 10 minutes
concentrationThe cooled solution is concentrated in vacuo
customthe residue purified by flash chromatography
washeluting with 10

Sources & evidence

ORD record: ord-db365b1b154c40bf87895d651f63fd1d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362294B2

Reaction notes

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