Bromine → HCID 13321947, compound

HRID 1284894Notes

Reaction equation

HRID 1284894 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].[Br:19]Br>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([Br:19])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 24408BromineHCID 13321936HCID 13321936, compound

Product 1

HCID 13321947HCID 13321947, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

A solution is prepared from 1.15 g of 5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (Example 3) in 50 ml of chloroform and 5.3 ml of pyridine and combined dropwise with 1 g (0.33 ml) of bromine in 10 ml of chloroform at room temperature. After 6 hours of agitation, the mixture is concentrated, taken up in 30 ml of water, made alkaline with ammonia, layered over with ethyl acetate, and then shaken and suctioned off. The thus-obtained residue is 0.86 g of 8-bromo-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester, mp 286°-290° C. (under decomposition).

Workup

  1. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-fda5a674675c49e091d19f2df96fec58
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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