Water → HCID 66997876, compound

HRID 559170Notes

Reaction equation

HRID 559170 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[C:10]([O:12]C)[CH:9]=[CH:8][C:7]=1[C:14]1[C:32](=[O:33])[N:31]([CH3:34])[C:17]2[N:18]([CH3:30])[C:19]3[C:24]([C:16]=2[CH:15]=1)=[CH:23][C:22]([C:25]1[NH:26][N:27]=[CH:28][CH:29]=1)=[CH:21][CH:20]=3.O>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:7]=1[C:14]1[C:32](=[O:33])[N:31]([CH3:34])[C:17]2[N:18]([CH3:30])[C:19]3[C:24]([C:16]=2[CH:15]=1)=[CH:23][C:22]([C:25]1[NH:26][N:27]=[CH:28][CH:29]=1)=[CH:21][CH:20]=3

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 66998150HCID 66998150, compound

Product 1

HCID 66997876HCID 66997876, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −78° C., a 1M solution of BBr3 in CH2Cl2 (2.19 ml, 2.19 mmol) is added to a solution of compound E 3-(2-chloro-4-methoxyphenyl)-1,9-dimethyl-6-(2H-pyrazol-3-yl)-1,9-dihydropyrido[2,3-b]indol-2-one (306 mg, 0.73 mmol) in 3 ml of CH2Cl2. The mixture is stirred at AT for 16 h. H2O is added and the precipitate is filtered off. The solid is taken up in MeOH/CH2Cl2 and the product is adsorbed onto silica. Purification is carried out by column chromatography, elution being carried out with CH2Cl2/5% MeOH. The residue is taken up with MeOH, and the product is washed and filtered with MeOH.

Workup

  1. filtrationthe precipitate is filtered off
  2. customPurification
  3. washis carried out by column chromatography, elution
  4. washthe product is washed
  5. filtrationfiltered with MeOH

Sources & evidence

ORD record
ord-e6a35aa13ce34771bb733f6e7892af17
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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