Ammonia → HCID 18182456, compound

HRID 1359323Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)(=O)=O.[C:25]([C:27]1([OH:35])[CH:32]2[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]2)[CH2:28]1)#[CH:26].C(N(CC)CC)C.N>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:8]2[C:7]([C:26]#[C:25][C:27]3([OH:35])[CH:32]4[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]4)[CH2:28]3)=[CH:12][CH:11]=[C:10]([CH3:13])[N:9]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 230 mg of 2-(4-methoxybenzyl)-6-methyl-3-pyridyl trifluoromethane sulfonate, 116 mg of 3-ethynyl-3-quinuclidinol, 147 mg of tetrakis(triphenylphosphine)palladium(0), 24 mg of cuprous iodide, 266 μl of triethylamine and 5.0 ml of N,N-dimethylformamide was heated under stirring at 80° C. for 3 hours in a nitrogen atmosphere. The reaction solution was poured into aqueous dilute ammonia, and the mixture was extracted with ethyl acetate. Then, the organic phase was washed with brine and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane/ethyl acetate (1:1) and then with ethyl acetate/methanol (20:1), to give 192 mg of the target compound.

Workup

temperaturewas heated
extractionthe mixture was extracted with ethyl acetate
washThen, the organic phase was washed with brine
customthe solvent was removed
washeluted with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record: ord-759f5649aa2345908e6a954906f60f4f
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599917B1

Reaction notes

Loading…