Cesium carbonate → HCID 117600326, compound

HRID 1505582Notes

Reaction equation

HRID 1505582 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([NH2:6])=[O:5].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:63]1[CH:68]=[CH:67][CH:66]=[C:65]([CH2:69][C:70]([F:73])([F:72])[F:71])[CH:64]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([NH:6][C:67]1[CH:68]=[CH:63][CH:64]=[C:65]([CH2:69][C:70]([F:71])([F:73])[F:72])[CH:66]=1)=[O:5]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 10419858HCID 10419858, compoundHCID 113907871-bromo-3-(2,2,2-trifluoroethyl)benzene

Product 1

HCID 117600326HCID 117600326, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen, to 2-fluoro-6-nitrobenzamide (921 mg, 5.00 mmol, 1.00 equiv) in dioxane (5.0 mL) at 23° C. was added palladium acetate (225 mg, 1.00 mmol, 0.200 equiv), Xantphos (868 mg, 1.50 mmol, 0.300 equiv), cesium carbonate (2.28 g, 7.00 mmol, 1.40 equiv), and 1-bromo-3-(2,2,2-trifluoroethyl)benzene (1.31 g, 5.50 mmol, 1.10 equiv). After stirring for 16 hr at 100° C., the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography eluting with EtOAc/hexanes to afford 860 mg of the title compound (50% yield).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography
  3. washeluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-bbba67cdeae14608a51bf17cc04451e1
Source dataset
uspto-grants-2015_12
Patent number
US09216985B2

Reaction notes

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