3-Chloroaniline → HCID 11610355, compound

HRID 1941756Notes

Reaction equation

HRID 1941756 reaction equation
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Cl[C:48]1[CH:53]=[C:52]([C:54]2[CH:59]=[CH:58][N:57]=[C:56]([NH:60][CH:61]([CH3:65])[CH2:62][O:63][CH3:64])[CH:55]=2)[CH:51]=[CH:50][N:49]=1.[Cl:66][C:67]1[CH:68]=[C:69]([CH:71]=[CH:72][CH:73]=1)[NH2:70].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:66][C:67]1[CH:68]=[C:69]([NH:70][C:48]2[CH:53]=[C:52]([C:54]3[CH:59]=[CH:58][N:57]=[C:56]([NH:60][CH:61]([CH3:65])[CH2:62][O:63][CH3:64])[CH:55]=3)[CH:51]=[CH:50][N:49]=2)[CH:71]=[CH:72][CH:73]=1

Participants

7

Reactant 4

HCID 79323-ChloroanilineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 86610350HCID 86610350, compound

Product 1

HCID 11610355HCID 11610355, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Pd(OAc)2 (8 mg) and BINAP (16 mg) were suspended in toluene (10 ml) and stirred under argon for 10 mins, then (2′-Chloro-[4,4′]bipyridinyl-2-yl)-(2-methoxy-1-methyl-ethyl)-amine (90 mg), 3-chloroaniline (124 mg) and potassium carbonate (890 mg) were added. The mixture was stirred at 110° C. for 5 hours then cooled to room temp, poured onto water and extracted with ethyl acetate, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by passing the crude mixture down Kieselgel using 1:99 THF:CH2Cl2 as the eluent.

Workup

  1. stirringThe mixture was stirred at 110° C. for 5 hours
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-e63edb7a70414072908744a424ee15be
Source dataset
uspto-grants-2013_03
Patent number
US08389442B2

Reaction notes

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