Isatoic Anhydride → 7-Bromo-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361364Notes

Reaction equation

[NH2:1][C:2]1[C:3]([CH3:25])=[C:4]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][C:16]([Br:21])=[CH:17][CH:18]=4)[NH:13][C:12]=3[C:11]([C:22]([NH2:24])=[O:23])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH:26]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29](=O)[O:28][C:27]1=O.[N+](O[La](O[N+]([O-])=O)O[N+]([O-])=O)([O-])=O.COC(OC)OC>O1CCCC1.C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>[Br:21][C:16]1[CH:15]=[C:14]2[C:19]([C:20]3[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([N:1]5[C:29](=[O:28])[C:30]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[N:26]=[CH:27]5)[C:3]=4[CH3:25])=[CH:9][N:10]=[C:11]([C:22]([NH2:24])=[O:23])[C:12]=3[NH:13]2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-(3-amino-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxamide (0.243 g, 0.615 mmol), 1H-benzo[d][1,3]oxazine-2,4-dione (0.251 g, 1.537 mmol), tris(nitrooxy)lanthanum, 6H2O (0.080 g, 0.184 mmol), and trimethoxymethane (2.020 mL, 18.44 mmol) in tetrahydrofuran (2 mL) was heated at 90° C. for 16 hr. The mixture was diluted with ethyl acetate (120 mL), washed with water (2×30 mL) and brine (30 mL), and dried over anhydrous MgSO4. The desired product (0.198 g, 0.378 mmol, 61.4% yield) was isolated as a yellow solid by ISCO (40 g silica gel, solid loading, 40-80% ethyl acetate/hexane).

Workup

washwashed with water (2×30 mL) and brine (30 mL)
dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record: ord-9bf7f83525814e0798cd3c5d610d3001
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

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