Carbon tetrabromide → HCID 57557953, compound

HRID 1162926Notes

Reaction equation

HRID 1162926 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13]([C@H:15]3[C@@H:19]([CH2:20]O)[O:18][C:17]([CH3:23])([CH3:22])[O:16]3)=[O:14])[CH:10]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[NH:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:54]>C(Cl)Cl>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13]([C@H:15]3[C@@H:19]([CH2:20][Br:54])[O:18][C:17]([CH3:23])([CH3:22])[O:16]3)=[O:14])[CH:10]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[NH:3]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57558215HCID 57558215, compound

Product 1

HCID 57557953HCID 57557953, compoundYield 176.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The (4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-carboxylic acid [1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]amide (1.5 g, 3.24 mmol) obtained in step A was dissolved in an anhydrous methylene chloride solution (30 ml). Thereafter, triphenylphosphine (2.21 g, 8.43 mmol) and carbon tetrabromide (2.80 g, 8.43 mmol) were added to the solution, and the obtained mixture was stirred at a room temperature for 3 hours. Thereafter, the solvent was distilled away. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1), so as to obtain (4R,5S)-5-bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-carboxylic acid [1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]amide (3.0 g).

Workup

  1. distillationThereafter, the solvent was distilled away
  2. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1)

Sources & evidence

ORD record
ord-558a9b73b7ca42afa0e23b8b774ea54b
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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