Isopropyl iodide → (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isopropyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898234Notes

Reaction equation

HRID 898234 reaction equation
[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:23])[CH:10]=2)[NH:5][C:4]1=[O:24])[CH3:2].[CH:25](I)([CH3:27])[CH3:26].C(N1C2C(=CC(F)=CC=2)N(C(=O)C2C=CC=C(OC)C=2)[C@H](CC)C1=O)C>>[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:23])[CH:10]=2)[N:5]([CH:25]([CH3:27])[CH3:26])[C:4]1=[O:24])[CH3:2]

Participants

4

Reactant 3

HCID 6362Isopropyl iodideHCID 69223657(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneHCID 69223676(3R)-1,3-diethyl-6-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 69221297(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isopropyl-3,4-dihydroquinoxalin-2(1H)-oneYield 54%

Procedure

(3R)-3-Ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 8) was treated with isopropyl iodide at reflux according to the procedure for the preparation of (3R)-1,3-diethyl-6-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 8) to yield (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isopropyl-3,4-dihydroquinoxalin-2(1H)-one (54%). MS (ESI) m/z 371 ([M+H]+).

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-0198c057adaf4d92b5b593a1d2a95a9a
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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