Toluene → HCID 66662290, compound

HRID 2275570Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([N:14]3[CH2:18][CH2:17][C@@:16]4([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[C:20](=[O:27])[O:19]4)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:28]1[CH2:32][CH2:31][NH:30][C:29]1=[O:33].C1(C)C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>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]>[O:33]=[C:29]1[N:30]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:12]([N:14]4[CH2:18][CH2:17][C@@:16]5([C:22]6[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=6[C:20](=[O:27])[O:19]5)[CH2:15]4)=[O:13])[CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH2:31][CH2:32][O:28]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (1R)-1′-{[1-(4-bromophenyl)cyclobutyl]carbonyl}-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (20.7 mg, 0.0000485 mol) and oxazolidin-2-one (12.7 mg, 0.000146 mol) in freshly distilled toluene (0.34 mL, 0.0032 mol), were added tris(dibenzylidene acetone)dipalladium(0) (4.4 mg, 0.0000048 mol), tri-tert-butylphosphine (2.0 mg, 0.0000097 mol) and cesium carbonate (15.8 mg, 0.0000485 mol), and the mixture was heated to 50° C. overnight. The reaction mixture then was cooled to rt, filtered over celite and concentrated under reduced pressure. The crude product was purified by prep-HPLC. LC/MS (M+H) 433.2.

Workup

temperatureThe reaction mixture then was cooled to rt
filtrationfiltered over celite and
concentrationconcentrated under reduced pressure
customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-e6c1c8ab8a3e456fa4b93cad26b021a7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126927B2

Reaction notes

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