5-Bromoisatin → 8-Bromoindolo[2,1-b]quinazoline-6,12-dione

HRID 1756566Notes

Reaction equation

HRID 1756566 reaction equation
Cl[C:2]1[CH:13]=[C:6]2[C:7](OC(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=O)[C:18]2=[O:25].FC1C=C2C(=CC=1)NC(=O)C2=O>>[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]1[C:19](=[N:11][C:5]3[C:6]([C:7]1=[O:8])=[CH:13][CH:2]=[CH:3][CH:4]=3)[C:18]2=[O:25]

Participants

4

Reactant 3

HCID 68895-BromoisatinHCID 784805-Chloroisatoic anhydrideHCID 2365665-Fluoroisatin

Product 1

HCID 4785728-Bromoindolo[2,1-b]quinazoline-6,12-dioneYield 9%

Procedure

Using the procedure in Example 12 and substituting isatoic anhydride for 5-chloroisatoic anhydride and 5-bromoisatin for 5-fluoroisatin gave the title compound in 9% yield: mp 288°-290.2° C.; 1H NMR (300 MHz, CDCl3) δ 8.56 (d, 1H) 8.44 (d, 1H) 8.06 (s, 1H) 8.04 (s, 1H) 7.82-7.96 (m, 2H) 7.66-7.76 (m, 1H); MS (M+H)+ 328.

Sources & evidence

ORD record
ord-faa0b8283f7c4b31b405c8958c5f3fea
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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