Aniline → HCID 59174316, compound

HRID 1481673Notes

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.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([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[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

Conditions

Temperature: 110 °C

Procedure

A mixture of 4 (0.3 g, 1.52 mmol), 5 (0.61 g, 1.8 mmol), Pd(OAc)2 (0.017 g, 0.076 mmol), BINAP (0.066 g, 0.106 mmol) and Cs2CO3 (1.23 g, 3.78 mmol) in degassed toluene (20 mL) (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, washed with water and brine and dried over Na2SO4. Filtration followed by concentration under reduced pressure offered a residue which was further purified by column chromatography (SiO2, petroleum ether:ethyl acetate; 6:4) to obtain 6 (0.3 g, 39.5%) as a brown solid.

Workup

temperatureThe reaction mixture was cooled
washwashed with water and brine
dry with materialdried over Na2SO4
filtrationFiltration
concentrationfollowed by concentration under reduced pressure
customwas further purified by column chromatography (SiO2, petroleum ether:ethyl acetate; 6:4)

Sources & evidence

ORD record: ord-e7ee642caac7453eae337c7d1548d5ce
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409921B2

Reaction notes

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