Water → HCID 58118494, compound

HRID 1182841Notes

Reaction equation

HRID 1182841 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Br:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([NH2:14])=[O:13].[O:15]=[C:16](Cl)OC(Cl)(Cl)Cl.O>O1CCOCC1>[Br:11][C:7]1[CH:8]=[CH:9][C:10]2[C:2]3[NH:1][C:16](=[O:15])[NH:14][C:12](=[O:13])[C:3]=3[NH:4][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 58118513HCID 58118513, compound

Product 1

HCID 58118494HCID 58118494, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12.2 g (58 mmol) 3-amino-6-bromo-1H-indole-2-carboxylic acid amide was suspended in 50 ml dioxan, and, after the addition of 11.7 ml (96 mmol) diphosgene, the suspension was refluxed for 2 h. Having cooled down to room temperature, 20 ml water was carefully added and the precipitate was subsequently sucked off. 13.4 g (99%) 7-bromo-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione was obtained. ESI-MS [m/z]: 278, 280 [M−H]−

Workup

  1. temperaturethe suspension was refluxed for 2 h

Sources & evidence

ORD record
ord-7711214c0e95467bbc5cc5c39e37c62d
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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