Carbon tetrabromide → HCID 68514522, compound

HRID 1717391Notes

Reaction equation

HRID 1717391 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([NH:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[O:17])=[CH:12][CH:11]=2)[N:8]=[N:7][C:6]=1[C:24]([NH2:26])=[O:25].C1(P([C:40]2[CH:45]=[CH:44]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:46]C(Br)(Br)Br>ClCCl>[Br:46][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([NH:18][CH2:19][C:20]([F:22])([F:21])[F:23])=[O:17])=[CH:14][CH:15]=2)[N:8]=[N:7][C:6]=1[C:24]([NH:26][CH:44]1[CH2:45][CH2:40]1)=[O:25]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57665111HCID 57665111, compound

Product 1

HCID 68514522HCID 68514522, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3-hydroxypropyl)-1-(4-{[(2,2,2-trifluoroethyl)amino]carbonyl}phenyl)-1H-1,2,3-triazole-4-carboxamide (381 mg, 0.93 mmol) obtained in Example 398 and triphenylphosphine (365 mg) in dichloromethane (12 ml) was added tetrabromomethane (460 mg), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column (hexane/ethyl acetate=20/1 to 2/5) to give the title compound as a colorless solid (219 mg, 50%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column (hexane/ethyl acetate=20/1 to 2/5)

Sources & evidence

ORD record
ord-6bc6c0c2213d4403a1df2e92fc6bd5f3
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…