Potassium Iodide → (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-pentyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898238Notes

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].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[I-].[K+].C([C@H]1N(C(=O)C2C=CC=C(OC)C=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][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]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:4]1=[O:24])[CH3:2]

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 80571-Bromopentane

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

HCID 69223657(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 69221459(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-pentyl-3,4-dihydroquinoxalin-2(1H)-oneYield 55%

Procedure

(3R)-3-Ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 8) was treated with 1-bromopentane and potassium iodide (1.2 eq) according to the procedure for the preparation of (3R)-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one (see Example 4) to yield (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-pentyl-3,4-dihydroquinoxalin-2(1H)-one (55%). MS (ESI) m/z 399 ([M+H]+).

Sources & evidence

ORD record: ord-6941983561fa4be4ac8a22b4ff0e8813
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351709B2

Reaction notes

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