Carbon tetrabromide → HCID 66636851, compound

HRID 469225Notes

Reaction equation

HRID 469225 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:28])[C:13]([CH2:23][CH2:24][CH2:25][CH2:26]O)=[CH:14][N:15]3[CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:10][C:9]=2[F:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:50].C(=O)([O-])O.[Na+]>ClCCCl>[Br:50][CH2:26][CH2:25][CH2:24][CH2:23][C:13]1[C:12](=[O:28])[C:11]2[C:16](=[CH:17][C:8]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:9]([F:29])[CH:10]=2)[N:15]([CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:14]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 66636989HCID 66636989, compound

Product 1

HCID 66636851HCID 66636851, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

199 mg of 7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-3-(4-hydroxybutyl)quinolin-4(1H)-one was dissolved in 11 ml of 1,2-dichloroethane, and 257 mg of triphenylphosphine and 405 mg of carbon tetrabromide were added at room temperature, followed by stirring for 15 minutes. Aqueous saturated sodium hydrogen carbonate was added to the reaction mixture, followed by extraction with chloroform, washing with aqueous saturated sodium chloride, drying over anhydrous sodium sulfate and then concentration under a reduced pressure. The resulting residue was purified by a chromatography to obtain 78 mg of 3-(4-bromobutyl)-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washwashing with aqueous saturated sodium chloride
  3. dry with materialdrying over anhydrous sodium sulfate
  4. concentrationconcentration under a reduced pressure
  5. customThe resulting residue was purified by a chromatography

Sources & evidence

ORD record
ord-a64057a2e7464dc297b63b6662f8015b
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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