Water → HCID 68294880, compound

HRID 1854111Notes

Reaction equation

HRID 1854111 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=4)[CH:11]=[C:10]([C:23]([NH:25][CH2:26][C:27]4[C:28](=[O:35])[NH:29][C:30]([CH3:34])=[CH:31][C:32]=4[CH3:33])=[O:24])[C:9]=3[CH:8]=[N:7]2)[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:56].O>C(Cl)Cl>[Br:56][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[CH:11]=[C:10]([C:23]([NH:25][CH2:26][C:27]3[C:28](=[O:35])[NH:29][C:30]([CH3:34])=[CH:31][C:32]=3[CH3:33])=[O:24])[C:9]3[CH:8]=[N:7][N:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[C:14]=3[CH:13]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68294923HCID 68294923, compound

Product 1

HCID 68294880HCID 68294880, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(4-(hydroxymethyl)phenyl)-1H-indazole-4-carboxamide (1.5 g, 3.2 mmol) in DCM (20 mL), triphenyl phosphine (1.33 g, 5.10 mmol) was added and stirred at room temperature for 10 min. CBr4 (1.69 g, 5.10 mmol) was then added portion-wise to it and the resulting solution stirred at room temperature overnight. After completion, water was added and extraction was carried out using DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to give 6-(4-(bromomethyl)phenyl)-1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide (1.0 g, 58.8%).

Workup

  1. stirringthe resulting solution stirred at room temperature overnight
  2. extractionextraction
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude material which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a4e13373d64f441eb7a45bd5e598ec79
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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