Carbon tetrabromide → HCID 68295246, compound

HRID 1853986Notes

Reaction equation

HRID 1853986 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]2[CH:30]=[N:29][N:28]([CH:31]([CH3:33])[CH3:32])[C:16]=2[N:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26]O)[CH:21]=2)[CH:19]=1)=[O:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:54]>C(Cl)Cl>[Br:54][CH2:26][C:22]1[CH:21]=[C:20]([C:18]2[CH:19]=[C:14]([C:12]([NH:11][CH2:10][C:3]3[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])=[O:13])[C:15]3[CH:30]=[N:29][N:28]([CH:31]([CH3:32])[CH3:33])[C:16]=3[N:17]=2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68295298HCID 68295298, compound

Product 1

HCID 68295246HCID 68295246, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(3-(hydroxymethyl)phenyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.45 g, 0.1.011 mmol) in a DCM (10 mL), PPh3 (0.477 g, 1.81 mmol) was added at 0° C. & then stirred for 5 min. After that CBr4 (0.636 g, 1.92 mmol) was added and stirred at room temperature for 1 hr. After completion of reaction, solid was filtered & washed with small amount of DCM to afford 0.30 g of pure desired product.

Workup

  1. stirringstirred at room temperature for 1 hr
  2. customAfter completion of reaction, solid
  3. filtrationwas filtered
  4. washwashed with small amount of DCM

Sources & evidence

ORD record
ord-91efba6ea1cc42579d3338e559c6bf39
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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