Dimethylformamide → HCID 57763487, compound

HRID 230822Notes

Reaction equation

[CH2:1]([C:3]([C:13]1[CH:26]=[CH:25][C:16]([O:17][CH2:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:15]([CH3:27])[CH:14]=1)([C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH3:28][N:29](C=O)C>CCOCC.[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:21][C:20]([CH3:23])([CH3:22])[C:19](=[O:24])[CH2:18][O:17][C:16]1[CH:25]=[CH:26][C:13]([C:3]([C:6]2[CH:11]=[CH:10][C:9]([C:28]#[N:29])=[CH:8][CH:7]=2)([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:14][C:15]=1[CH3:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 1-{4-[1-ethyl-1-(4-iodo-phenyl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (3.0 g 6.27 mmol) and DMF (30 mL) is added Zn(CN)2 (0.44 g, 3.76 mmol), Pd2(dba)3 (0.29 g, 0.31 mmol), and DPPF (0.42 g, 0.75 mmol). The solution is heated at 100° C. overnight, diluted with Et2O (200 mL), washed with 4:1:4 sat NH4Cl:Conc. NH4OH:water (100 mL), water (100 mL), brine (100 mL), dried MgSO4, filtered and concentrated. The residue is purified by ISCO (10%-2-% EtOAc gradient) to furnish the title compound (1.1 g, 2.91 mmol, 46%).

Workup

washwashed with 4:1:4
filtrationNH4OH:water (100 mL), water (100 mL), brine (100 mL), dried MgSO4, filtered
concentrationconcentrated
customThe residue is purified by ISCO (10%-2-% EtOAc gradient)

Sources & evidence

ORD record: ord-117d97ad2da445f396678b70b937c19e
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566803B2

Reaction notes

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