Water → HCID 57672475, compound

HRID 2101749Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([O:7][CH3:8])=[O:6].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2[C:37]2[C:42]([O:43][CH3:44])=[CH:41][CH:40]=[CH:39][C:38]=2OC)CCCCC1.[OH2:53].[C:54]1(C)[CH:59]=CC=[CH:56][CH:55]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:59]([O:53][C:39]1[CH:40]=[CH:41][C:42]([O:43][CH3:44])=[CH:37][C:38]=1[C:2]1[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1)[CH2:54][CH2:55][CH3:56]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of methyl 3-bromo-4-tert-butylbenzoate (120 mg, 443 μmol), compound C.3 (226 mg, 664 μmol), potassium phosphate (282 mg, 1328 μmol), 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (36 mg, 89 μmol) (Aldrich, CAS# 657408-07-6), and tris(dibenzylideneacetone)dipalladium(0) (20 mg, 22 μmol) in toluene (1.0 mL) was stirred overnight at 110° C. The mixture was cooled to room temperature, filtered through a pad of celite with EtOAc rinsings, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford compound C.4 (63 mg, 39% yield) as a colorless oil. MS ESI (pos.) m/e: 388 (M+H2O), 393 (M+Na).

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered through a pad of celite with EtOAc rinsings
concentrationconcentrated
customThe crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)
customto afford compound C.4 (63 mg, 39% yield) as a colorless oil

Sources & evidence

ORD record: ord-709066a29d5249e5935fccfd4e5765d9
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572934B2

Reaction notes

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