Carbon tetrabromide → HCID 68295441, compound

HRID 1909168Notes

Reaction equation

HRID 1909168 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][C:23]([CH2:26]O)=[CH:22][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:23]1[CH:22]=[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]([CH3:33])[CH3:32])[C:16]=3[N:17]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68295072HCID 68295072, compound

Product 1

HCID 68295441HCID 68295441, compoundYield 52.9%

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-(4-(hydroxymethyl)phenyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.45 g, 1.01 mmol) in a DCM (10 mL) was added PPh3 (0.477 g, 1.81 mmol) at 0° C. & then stirred for 5 min. After that CBr4 (0.636 g, 1.92 mmol) was added & stirred at room temperature for 1 hr. After completion of reaction, turbid reaction mass was filtered & washed with small amount of DCM to afford the desired product as white solid (0.27 g, 52.9%).

Workup

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

Sources & evidence

ORD record
ord-3ebf731f652e412a8ac12161d652c5b4
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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