Toluene → HCID 178474043, compound

HRID 480477Notes

Reaction equation

BrC1C=C2[C:9](=CC=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=C2.[C:41](=[NH:54])(C1C=CC=CC=1)[C:42]1C=CC=CC=1.CC(C)([O-:58])C.[Na+].[C:61]1(C)[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>C(OCC)(=O)C.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=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:16][C:12]([C:7]1[CH:6]=[C:64]2[C:63](=[CH:9][CH:8]=1)[CH:62]=[C:61]([NH:54][C:41](=[O:58])[CH3:42])[CH:66]=[CH:65]2)([C:17]1[N:18]=[CH:19][NH:20][CH:21]=1)[CH:13]([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(6-bromo-naphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (14.0 g), benzophenone imine (5.18 g), tris(dibenzylideneacetone)dipalladium (440 mg), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (872 mg) and sodium t-butoxide (5.72 g) in toluene (140 ml) was heated at 80° C. for 18 h under argon atmosphere. After cooling, the mixture was diluted with ethyl acetate, filtered with celite pad. The filtrate was concentrated and the residue was chromatographed on silica gel (eluent; hexane:THF=1:1) followed by crystallization from hexane-THF (4:1) to give yellow titled compound (14.3 g).

Workup

temperatureAfter cooling
filtrationfiltered with celite pad
concentrationThe filtrate was concentrated
customthe residue was chromatographed on silica gel (eluent; hexane:THF=1:1)
customfollowed by crystallization from hexane-THF (4:1)

Sources & evidence

ORD record: ord-234d976244c044abb824a619305a0563
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649643B1

Reaction notes

Loading…