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

HRID 2201301Notes

Reaction equation

HRID 2201301 reaction equation
[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=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].BrC1C=CC=C([F:34])C=1>>[F:34][C:17]1[CH:16]=[C:15]([C:14]2[N:13]3[C:8]([C:9](=[O:23])[CH2:10][CH2:11][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:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 140821-Bromo-3-fluorobenzeneHCID 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 867235335-(3-Fluorophenyl)-1,3-dimethyl-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).

Sources & evidence

ORD record
ord-4baaf0c355b54305843d467f6c9f1b02
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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