1-Bromo-3-fluorobenzene → 5-(3-Fluorophenyl)-1,3,8-trimethyl-8,9-dihydropyrimido[4,5-a]indolizine-2,4,10(1H,3H,7H)-trione

HRID 2201303Notes

Reaction equation

HRID 2201303 reaction equation
[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14](C4C=C(C=CC=4)C#N)=[C:6]2[C:5](=[O:24])[N:4]([CH3:25])[C:3]1=[O:26])[CH2:12][CH2:11][CH2:10][C:9]3=[O:23].Br[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1.Br[CH2:36]CCC(OC)=O.BrCC(C)CC(OC)=O>>[F:34][C:30]1[CH:29]=[C:28]([C:14]2[N:13]3[C:8]([C:9](=[O:23])[CH2:10][CH:11]([CH3:36])[CH2:12]3)=[C:7]3[N:2]([CH3:1])[C:3](=[O:26])[N:4]([CH3:25])[C:5](=[O:24])[C:6]=23)[CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 4

HCID 140821-Bromo-3-fluorobenzeneHCID 107604Methyl 4-bromobutyrateHCID 14104192Methyl 4-bromo-3-methylbutanoate2×HCID 867234273-(1,3-Dimethyl-2,4,10-trioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

Product 1

HCID 867235345-(3-Fluorophenyl)-1,3,8-trimethyl-8,9-dihydropyrimido[4,5-a]indolizine-2,4,10(1H,3H,7H)-trione

Procedure

The title compound was prepared analogously to 3-(1,3-dimethyl-2,4,10-trioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile (Example 9 steps 1-7) by replacing 3-bromobenzonitrile (step 3) with 1-bromo-3-fluorobenzene (commercially available) and methyl 4-bromobutanoate (Step 5) with methyl 4-bromo-3-methylbutanoate (Intermediate T).

Sources & evidence

ORD record
ord-fd433ea5f5024f5baa9250108018edbd
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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