Bismuth trichloride → HCID 178451897, compound

HRID 923416Notes

Reaction equation

HRID 923416 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:19][C:20]2[CH:40]=[CH:39][C:23]3[NH:24][C:25]([C@@H:27]4[CH2:31][CH2:30][CH2:29][N:28]4[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[N:26][C:22]=3[CH:21]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Bi](Cl)(Cl)Cl.[BH4-].[Na+]>C(O)C>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:8]([CH2:19][C:20]2[CH:40]=[CH:39][C:23]3[NH:24][C:25]([C@@H:27]4[CH2:31][CH2:30][CH2:29][N:28]4[C:32]([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33])=[N:26][C:22]=3[CH:21]=2)[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24591Bismuth trichlorideHCID 4311764Sodium borohydrideHCID 178451900HCID 178451900, compound

Product 1

HCID 178451897HCID 178451897, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 99C (0.67 g, 1.23 mmol) was dissolved in ethanol (15 mL) and cooled in an ice bath. Bismuth trichloride (0.245 mL, 3.68 mmol) was added and a slurry formed to which was added sodium borohydride (0.743 g, 19.7 mmol) portionwise causing a black precipitate to form. This mixture was stirred at ambient temperature for 20 minutes, then re-cooled and quenched with methanol (2 mL), stirring for 10 min before filtering through celite. The filtrated was concentrated to give the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. customa slurry formed to which
  3. customto form
  4. temperaturere-cooled
  5. customquenched with methanol (2 mL)
  6. stirringstirring for 10 min
  7. filtrationbefore filtering through celite
  8. concentrationThe filtrated was concentrated

Sources & evidence

ORD record
ord-656e9b54bdb2440d8e5b54430d800435
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

Loading…