Water → HCID 58118527, compound

HRID 1182837Notes

Reaction equation

HRID 1182837 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:11])[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:8]1[CH:7]=[CH:6][C:5]2[NH:4][C:3]3[C:12](=[O:13])[NH:14][C:16](=[O:15])[NH:1][C:2]=3[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 58118508HCID 58118508, compound

Product 1

HCID 58118527HCID 58118527, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.3 g (5.1 mmol) 3-amino-5-bromo-1H-indole-2-carboxylic acid amide was suspended in 50 ml dioxan and, after the addition of 670 μl (5.5 mmol) diphosgene, refluxed for 2 h. Having cooled down to room temperature, 2 ml water was carefully added and thereafter the precipitate was sucked off. 1.4 g (94%) 8-bromo-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione was obtained. ESI-MS [m/z]: 278, 280 [M−H]−

Workup

  1. temperaturerefluxed for 2 h

Sources & evidence

ORD record
ord-e25bc8d062a2494897bca2e42db174a8
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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