Triethylamine → HCID 67265462, compound

HRID 1685826Notes

Reaction equation

Br[C:2]1[C:3]([CH:16]=[C:17]2[CH:21]([OH:22])[CH2:20][CH2:19][S:18]2)=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[CH:7]=1.C([O-])=O.[NH4+].C(N(CC)CC)C>COCCOC.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>[OH:22][CH:21]1[CH2:20][CH2:19][S:18][C:17]1=[CH:16][C:3]1[CH:2]=[CH:7][C:6]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[C:5]([O:14][CH3:15])[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-[5-bromo-4-(3-hydroxythiolan-2-ylidenemethyl)-2-methoxyphenyl]propionate (50 mg) obtained in Example 50 was dissolved in ethylene glycol dimethyl ether (2 ml), and then to the solution was added ammonium formate (25 mg), triethylamine (0.1 ml) and tetrakis(triphenylphosphine)palladium (50 mg). The mixture was stirred overnight at 80° C. in an argon atmosphere. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give the title compound (30 mg, 72%).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-c080134560564f7d9a0fb94d6cf3803d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148421B2

Reaction notes

Loading…