(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one → (3R)-3-ethyl-7-fluoro-4-(3-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898218Notes

Reaction equation

HRID 898218 reaction equation
[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([F:23])=[CH:9][CH:10]=2)[N:5]([CH3:24])[C:4]1=[O:25])[CH3:2].C([C@H]1N(C(=O)C2C=CC(O)=CC=2)C2C(=CC(F)=CC=2)N(C)C1=O)C>>[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([F:23])=[CH:9][CH:10]=2)[N:5]([CH3:24])[C:4]1=[O:25])[CH3:2]

Participants

3

Reactant 2

HCID 11709655(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69221291(3R)-3-Ethyl-7-fluoro-4-(3-methoxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 11544430(3R)-3-ethyl-7-fluoro-4-(3-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-oneYield 72%

Procedure

(3R)-3-Ethyl-7-fluoro-4-(3-methoxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one was treated according to the procedure for the preparation of (3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one (see Example 1) to give an oil which was purified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 40% EtOAc/hexane) to yield (3R)-3-ethyl-7-fluoro-4-(3-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one (72%). [α]D25=−281° (c=0.0098 G/ML, CHCl3); MS (ESI) m/z 329 ([M+H]+); MS (ESI) m/z 327 ([M−H]−) HRMS: calcd for C18H17FN2O3.0.10H2O, 329.9234; found (ESI+), 329.12884; Anal. Calcd for C18H17FN2O3 0.10H2O: C, 65.49; H, 5.25; N, 8.49. Found: C, 65.29; H, 4.93; N, 8.33.

Workup

  1. customto give an oil which
  2. customwas purified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-e48beed1c33e4ce998abbe4851171691
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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