Bromine → HCID 68420378, compound

HRID 1610150Notes

Reaction equation

HRID 1610150 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[N:10]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])O.[Na+].[Br:42]Br>ClCCl>[Br:42][C:15]1[C:14]([NH2:17])=[CH:13][CH:12]=[C:11]2[C:16]=1[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[N:9][N:10]2[C:18]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 68420167HCID 68420167, compound

Product 1

HCID 68420378HCID 68420378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A total of 1.04 g of. 3-(3-fluoro-phenyl)-1-trityl-1H-indazol-5-ylamine was dissolved in 22.3 ml of dichloromethane, and 375 mg of sodium hydrogencarbonate was added. Under ice-cooling and stirring, a solution of 0.12 ml of bromine in 50 ml dichloromethane was added dropwise over 50 minutes. After stirring for 2 hours while ice-cooling, saturated aqueous sodium thiosulfate solution and the mixture was extracted with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:5), to give 1.18 g of the title compound as a white foam.

Workup

  1. temperatureUnder ice-cooling
  2. stirringAfter stirring for 2 hours while ice-
  3. temperaturecooling
  4. extractionsaturated aqueous sodium thiosulfate solution and the mixture was extracted with diethyl ether
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified
  9. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-1829b4707db74a8dbef9d846bd0dfac2
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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