Formic Acid → HCID 178485298, compound

HRID 480456Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([OH:45])([C:21]3[N:22]=[CH:23][N:24](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:25]=3)[CH:18]([CH3:20])[CH3:19])[CH:13]=2)[C:8]=1[C:46]([NH:48][CH3:49])=[O:47])(=O)=O.C(O)=O.C(N(CCCC)CCCC)CCC.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:45][C:17]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:46]([NH:48][CH3:49])=[O:47])=[CH:7][CH:16]=[CH:15]2)([C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)[CH:18]([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-1-(methylaminocarbonyl)-2-naphthyl trifluoromethanesulfonate (700 mg), formic acid (0.1 mL), tributylamine (1.0 mL), dichlorobis(triphenylphosphine)palladium (70 mg), and 1,3-bis-(diphenylphosphino)propane (103 mg) in anhydrous DMF (5 mL) was heated at 80° C. for 4 h. After dilution with water, the yellow precipitate was filtered and washed with water. The precipitate was purified by flash column chromatography on silica gel (hexane:AcOEt=3:2→1:1) to give the title compound (384 mg) as a colorless amorphous powder.

Workup

filtrationAfter dilution with water, the yellow precipitate was filtered
washwashed with water
customThe precipitate was purified by flash column chromatography on silica gel (hexane:AcOEt=3:2→1:1)

Sources & evidence

ORD record: ord-f26ca32b2b704818a3a9ba0177ff5d15
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649643B1

Reaction notes

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