Water → 7-bromo-9-fluoro-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione

HRID 1182829Notes

Reaction equation

HRID 1182829 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Br:12])=[CH:8][C:9]=2[F:11])[NH:4][C:3]=1[C:13]([NH2:15])=[O:14].[O:16]=[C:17](Cl)OC(Cl)(Cl)Cl.O>O1CCOCC1>[Br:12][C:7]1[CH:8]=[C:9]([F:11])[C:10]2[C:2]3[NH:1][C:17](=[O:16])[NH:15][C:13](=[O:14])[C:3]=3[NH:4][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 581185403-amino-6-bromo-4-fluoro-1H-indole-2-carboxylic acid amide

Product 1

HCID 581185247-bromo-9-fluoro-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dioneYield 74.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

15.4 g (56.6 mmol) 3-amino-6-bromo-4-fluoro-1H-indole-2-carboxylic acid amide was suspended in 300 ml dioxan and after the addition of 7.5 ml (61.8 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. 12.5 g (74%) 7-bromo-9-fluoro-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione was obtained. ESI-MS [m/z]: 296, 298 [M−H]−

Workup

  1. temperaturewas refluxed for 2 h

Sources & evidence

ORD record
ord-443644189792448f8408bb58693d8b68
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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