Water → HCID 68295385, compound

HRID 1854122Notes

Reaction equation

HRID 1854122 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][CH2:24]O)[CH:16]=4)[CH:11]=[C:10]([C:26]([NH:28][CH2:29][C:30]4[C:31](=[O:38])[NH:32][C:33]([CH3:37])=[CH:34][C:35]=4[CH3:36])=[O:27])[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:59].O>C(Cl)Cl>[Br:59][CH2:24][CH2:23][CH2:22][O:21][C:17]1[CH:16]=[C:15]([C:12]2[CH:11]=[C:10]([C:26]([NH:28][CH2:29][C:30]3[C:31](=[O:38])[NH:32][C:33]([CH3:37])=[CH:34][C:35]=3[CH3:36])=[O:27])[C:9]3[CH:8]=[N:7][N:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[C:14]=3[CH:13]=2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68295447HCID 68295447, compound

Product 1

HCID 68295385HCID 68295385, compoundYield 71.3%

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-(3-(3-hydroxypropoxy)phenyl)-1H-indazole-4-carboxamide (0.35 g, 0.68 mmol) in DCM (5 mL), triphenyl phosphine (0.285 g, 1.08 mmol) was added and the reaction mixture stirred at room temperature for 10 min. Finally CBr4 (0.36 g, 1.08 mmol) was added portion wise and resulting solution was stirred at room temperature for 4 h. On completion, water was added to the reaction mixture and extracted with 5% MeOH/DCM. The combined organic layer was dried over sodium sulfate and concentrated to give crude material which was purified by column chromatography over silica gel to afford 6-(3-(3-bromopropoxy)phenyl)-1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide (0.28 g, 71%).

Workup

  1. customresulting solution
  2. stirringwas stirred at room temperature for 4 h
  3. extractionextracted with 5% MeOH/DCM
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto give crude material which
  7. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-f2457d63990540f1a360448ad23e2407
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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