Potassium Iodide → (3R)-1-benzyl-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 898219Notes

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][CH3:21])[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([F:23])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:24])[CH3:2].[I-].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N1C2C(=CC=C(F)C=2)N(C(=O)C2C=CC(OC)=CC=2)[C@H](CC)C1=O)C1C=CC=CC=1>>[CH2:27]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([F:23])[CH:7]=2)[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C@H:3]([CH2:1][CH3:2])[C:4]1=[O:24])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 7498Benzyl Bromide

HCID 69221447(3R)-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HCID 69223935(3R)-1-benzyl-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 69221455(3R)-1-benzyl-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneYield 85%

Procedure

(3R)-3-Ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 4) was treated with potassium iodide (5 eq) and benzyl bromide according to the procedure for the preparation of (3R)-1-benzyl-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 2) to yield (3R)-1-benzyl-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (85%).

Sources & evidence

ORD record: ord-3269d9d8ad434d96bc7b82032a1e8879
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351709B2

Reaction notes

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