Aniline → HCID 67227354, compound

HRID 2168326Notes

Reaction equation

HRID 2168326 reaction equation
Br[C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 7210837Methyl 2-bromo-4-fluorobenzoate

Product 1

HCID 67227354HCID 67227354, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Methyl 2-bromo-4-fluorobenzoate (1.00 g), aniline (0.47 mL), palladium(II) acetate (0.048 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.214 g) and Cs2CO3 (2.08 g) in toluene (12 mL) were stirred at 90° C. for 24 hours. The reaction was concentrated and chromatographed on silica gel with 5-50% ethyl acetate/hexanes.

Workup

  1. concentrationThe reaction was concentrated
  2. customchromatographed on silica gel with 5-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-85a9205da4f0418aaa5dbfe34703405e
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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