Carbon tetrabromide → HCID 18696595, compound

HRID 1870535Notes

Reaction equation

HRID 1870535 reaction equation
O[CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[N:8]1[C:12]([O:13][CH3:14])=[N:11][N:10]([CH3:15])[C:9]1=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[Br:37][CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[N:8]1[C:12]([O:13][CH3:14])=[N:11][N:10]([CH3:15])[C:9]1=[O:16]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18696591HCID 18696591, compound

Product 1

HCID 18696595HCID 18696595, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the title compound of Step E (2.6 g) in methylene chloride (20 mL) under N2 at room temperature was added sequentially triphenylphosphine (3.44 g) and carbon tetrabromide (5.58 g). The resulting orange solution was allowed to stir for 1 h at room temperature and was then concentrated under reduced pressure to give an orange oil. The residue was purified by flash chromatography (1:1 ethyl acetate:hexane as eluent) to afford 2.3 g of the title compound of Step F, a compound of the invention, as a white solid. 1H NMR (CDCl3): δ 7.34 (d,1H), 6.92 (d,1H), 4.65 (s,2H), 3.98 (s,3H), 3.45 (s,3H).

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. customto give an orange oil
  3. customThe residue was purified by flash chromatography (1:1 ethyl acetate:hexane as eluent)

Sources & evidence

ORD record
ord-c25b3c583bdf4279b1404e041421b025
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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