Cesium carbonate → Methyl 4-[(4E)-5-{5-fluoro-2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}-3-{2-[4-(methoxycarbonyl)phenyl]ethyl}pent-4-en-1-yl]benzoate

HRID 1512208Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+].[F:17][C:18]1[CH:19]=[CH:20][C:21]([OH:51])=[C:22](/[CH:24]=[CH:25]/[CH:26]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([O:49][CH3:50])=[O:48])=[CH:43][CH:42]=2)[CH2:27][CH2:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)[CH:23]=1>CN(C=O)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([O:51][CH2:2][CH2:3][CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][C:6]2=[O:10])=[C:22](/[CH:24]=[CH:25]/[CH:26]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([O:49][CH3:50])=[O:48])=[CH:43][CH:42]=2)[CH2:27][CH2:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

146 mg (0.91 mmol) of 1-(3-chloropropyl)pyrrolidin-2-one [CAS Reg. No. 91152-30-6] and 295 mg (0.91 mmol) of anhydrous cesium carbonate are added to a solution of 215 mg (0.45 mmol) of methyl 4-[(4E)-5-(5-fluoro-2-hydroxyphenyl)-3-{2-[4-(methoxycarbonyl)phenyl]ethyl}pent-4-en-1-yl]benzoate in 5 ml of dry DMF, and the mixture is then stirred at 60° C. for 12 h. The mixture is then filtered, and the filtrate is evaporated to dryness. The residue is purified by preparative HPLC. This gives 165 mg (purity 93%, 0.25 mmol, 56% of theory) of a colorless oil.

Workup

filtrationThe mixture is then filtered
customthe filtrate is evaporated to dryness
customThe residue is purified by preparative HPLC

Sources & evidence

ORD record: ord-aed9c35b54c4473b83f2ff2707b9741c
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217063B2

Reaction notes

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