Stannous Chloride → HCID 66933877, compound

HRID 1019603Notes

Reaction equation

HRID 1019603 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[C:13]([Br:22])=[C:14]([C:16](=O)[C:17]([F:20])([F:19])[F:18])[S:15][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+].Cl[Sn]Cl>CCO.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[C:13]([Br:22])=[C:14]([CH2:16][C:17]([F:20])([F:18])[F:19])[S:15][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 4311764Sodium borohydrideHCID 67197583HCID 67197583, compound

Product 1

HCID 66933877HCID 66933877, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The product of step (a) (73 mg, 0.18 mmol) was stirred in 3 mL EtOH and treated with NaBH4 (20 mg, 0.5 mmol). After stirring for 20 minutes, the reaction was quenched with HOAc until no bubbling was observed. The reaction was diluted with water (5 mL) and the crude product was extracted into DCM (3×5 mL). The combined organic extracts were concentrated and the residue was dissolved in HOAc (2 mL) and concentrated HCl (1 mL). SnCl2 (225 mg, 1 mmol) was added and the reaction was heated to 80° C. for 2 hours. The crude reaction was diluted with water (10 mL) and the product was extracted into DCM (3×5 mL). The combined organic extracts were concentrated to dryness and used without further purification.

Workup

  1. customthe reaction was quenched with HOAc until no bubbling
  2. additionThe reaction was diluted with water (5 mL)
  3. extractionthe crude product was extracted into DCM (3×5 mL)
  4. concentrationThe combined organic extracts were concentrated
  5. dissolutionthe residue was dissolved in HOAc (2 mL)
  6. customThe crude reaction
  7. extractionthe product was extracted into DCM (3×5 mL)
  8. concentrationThe combined organic extracts were concentrated to dryness
  9. customused without further purification

Sources & evidence

ORD record
ord-29926e1ec0c346f5a794cb967b43ca57
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Reaction notes

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