Bismuth trichloride → HCID 59540436, compound

HRID 923387Notes

Reaction equation

HRID 923387 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH:10]([CH3:12])[CH3:11])=[CH:6][CH:5]=1)([O-])=O.[Bi](Cl)(Cl)Cl.[BH4-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH:10]([CH3:12])[CH3:11])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 24591Bismuth trichlorideHCID 4311764Sodium borohydrideHCID 59540450HCID 59540450, compound

Product 1

HCID 59540436HCID 59540436, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product from Example 24A (42.8 mg, 0.130 mmol) in ethanol (1.3 mL) under a N2 atmosphere was added bismuth trichloride (0.026 mL, 0.39 mmol). The mixture was cooled in a cold-water bath, and sodium borohydride (79 mg, 2.079 mmol) was slowly added portion-wise over several minutes. When the addition was complete, the resulting mixture was stirred at rt for 1 hour, and then filtered through celite and rinsed with methanol. The filtrate was concentrated to ˜½ volume, diluted with 1:3 isopropyl alcohol:CH2Cl2, and washed with saturated aqueous NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (31.9 mg). MS (APCI) m/s 270.5 (M+H)+.

Workup

  1. temperatureThe mixture was cooled in a cold-water bath
  2. customover several minutes
  3. additionWhen the addition
  4. filtrationfiltered through celite
  5. washrinsed with methanol
  6. concentrationThe filtrate was concentrated
  7. additiondiluted with 1:3 isopropyl alcohol
  8. washCH2Cl2, and washed with saturated aqueous NaHCO3
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76391718eeb940afa5c4a2ac6b49bb21
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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