Triethylamine → HCID 46940198, compound

HRID 1095908Notes

Reaction equation

C(N(CC)CC)C.[CH:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)=[CH2:9].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:42]1[CH:47]=[CH:46][C:45]([CH:48]([CH3:62])[C:49]([C:55]2[CH:60]=[CH:59][N:58]=[C:57]([CH3:61])[CH:56]=2)([OH:54])[C:50]([F:53])([F:52])[F:51])=[C:44]([Cl:63])[CH:43]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:63][C:44]1[CH:43]=[C:42](/[CH:9]=[CH:8]/[C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH:47]=[CH:46][C:45]=1[CH:48]([CH3:62])[C:49]([OH:54])([C:55]1[CH:60]=[CH:59][N:58]=[C:57]([CH3:61])[CH:56]=1)[C:50]([F:52])([F:53])[F:51]

Participants

Conditions

Temperature: 100 °C

Procedure

Triethyl amine (0.02 ml), 4-vinylbenzoic acid (CAS Reg. No. 1075-49-6, 19 mg), tri-o-tolylphosphine (2 mg) and palladium acetate (1 mg) were added to a solution of 3-(4-bromo-2-chloro-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-ol (Example 60 step 1, 41 mg) in DMF (1 ml). The mixture was stirred at 100° C. for 3 h. Water was added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0->100% EtOAc/heptane) to give the title compound (28 mg) as an orange oil. MS (m/e)=476.1 [M+H+].

Workup

extractionextracted with EtOAc
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated to an oil
customThe residue was purified by flash chromatography (SiO2, 0->100% EtOAc/heptane)

Sources & evidence

ORD record: ord-c799905d34264b038860fd963472257f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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