4-Bromoisatin → 5-Bromoquinazoline-2,4(1H,3H)-dione

HRID 2036769Notes

Reaction equation

HRID 2036769 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[NH:6]2.[NH2:13]C1C=CC=C(Br)C=1C(N)=O.[N-]=C=O.[Na+]>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[NH:13][C:5](=[O:11])[NH:6]2

Participants

4

Reactant 3

HCID 45000124-BromoisatinHCID 11051568NaNCOHCID 67055862HCID 67055862, compound

Product 1

HCID 196042325-Bromoquinazoline-2,4(1H,3H)-dione

Procedure

Compounds of formula I may be synthesized according to Scheme 1. Commercially available 4-bromoindoline-2,3-dione may be hydrolyzed to 2-amino-6-bromobenzamide followed by condensation with sodium isocyanate to form 5-bromoquinazoline-2,4(1H,3H)-dione. The protocols include, but are not limited to, palladium mediated cross coupling between 5-bromoquinazoline-2,4(1H,3H)-dione and the aryl boronic acid or ester to form the intermediate 5-substituted quinazoline-2,4(1H, 3H)-dione. Conversion to the corresponding dichloro quinazoline and sequential displacement at the 4-position followed by transition metal mediated cross coupling or displacement of the C2 chloride forms compounds I as described.

Workup

  1. customCompounds of formula I may be synthesized

Sources & evidence

ORD record
ord-3f25f49a6c034ec8a67f805d044e903f
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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