Aniline → HCID 59174316, compound

HRID 1481670Notes

Reaction equation

HRID 1481670 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[O:12][C:13]1[C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=[C:15]([S:22][CH3:23])[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].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>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:26]=[CH:25][CH:24]=[C:11]([O:12][C:13]2[C:18]([C:19](=[O:21])[NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:17][N:16]=[C:15]([S:22][CH3:23])[N:14]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 6115AnilineHCID 10796Cesium carbonateHCID 59174529HCID 59174529, compound

Product 1

HCID 59174316HCID 59174316, compoundYield 65%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 4 (0.275 g, 1.19 mmol), 5 (0.403 g, 1.19 mmol), prepared according to Step-1 of Example 20, Pd(OAc)2 (0.0026 g, 0.11 mmol), BINAP (0.0037 g, 0.059 mmol) and Cs2CO3 (0.969 g, 2.95 mmol) in degassed toluene (toluene was purged with N2 for 30 min) was heated at 110° C. for 16 h under N2 atmosphere. The reaction mixture was cooled, diluted with EtOAc (20 mL), washed with water (10 mL), brine (10 mL) and dried over Na2SO4. Filtration followed by concentration under reduced pressure offered a residue which was further purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate 5/5) to give 6 (0.350 g, 55%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water (10 mL), brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration
  5. concentrationfollowed by concentration under reduced pressure
  6. customwas further purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate 5/5)

Sources & evidence

ORD record
ord-45e46e6a1a314d2bb3abee7fdb562551
Source dataset
uspto-grants-2016_08
Patent number
US09409921B2

Reaction notes

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