Sodium Carbonate → HCID 178450046, compound

HRID 480457Notes

Reaction equation

FC(F)(F)S(OC1C=C[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=1)(=O)=O.[C:48]1(B(O)O)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[Cl-].[Li+].C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[NH:24]1[CH:25]=[C:21]([C:17]([C:12]2[CH:11]=[CH:10][C:9]3[C:14](=[CH:14][CH:9]=[C:10]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[CH:11]=3)[CH:13]=2)([OH:45])[CH:18]([CH3:19])[CH3:20])[N:22]=[CH:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl trifluoromethanesulfonate (2.0 g), phenylboronic acid (446 mg), tetrakis(triphenylphosphine)-palladium (0) (115 mg) and lithium chloride (259 mg) were dissolved in dimethoxyethane (DME, 20 mL). Ag.Na2CO3 (2M, 4.5 mL) was added to the mixture, and whole was heated at 80° C. for 20 h. Water was added, the mixture was extracted with AcOEt. The extract was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluent, hexane:THF=2:1) to give the titled compound (1.50 g) as a pale yellow powder.

Workup

extractionthe mixture was extracted with AcOEt
washThe extract was washed with brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography (eluent, hexane:THF=2:1)

Sources & evidence

ORD record: ord-3f5a297594fe48ce9dd871548ff112a8
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649643B1

Reaction notes

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