Trifluoroacetic acid → HCID 68578649, compound

HRID 641624Notes

Reaction equation

HRID 641624 reaction equation
[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[S:12][CH:13]=[CH:14][C:4]=2[N:3]=1.[BH4-].[Na+].FC(F)(F)C(O)=O>O1CCOCC1>[CH3:1][CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[S:12][CH:13]=[CH:14][C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 68579044HCID 68579044, compound

Product 1

HCID 68578649HCID 68578649, compoundYield 132.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

5-Methylthieno[3,2-c]isoquinoline (12 g, 60 mmol) and sodium borohydride (9.0 g, 240 mmol) were combined in dry 1,4-dioxane (200 mL) at 23° C. Trifluoroacetic acid (9.2 mL, 120 mmol) was slowly added via syringe with gentle bubbling. After the addition was complete, the mixture was heated to reflux for 24 h. At this time the mixture was cooled to 23° C., quenched with de-gassed saturated aqueous sodium bicarbonate (450 mL) and extracted under nitrogen with de-gassed methylene chloride (3×ca. 150 mL). The combined extracts were washed under nitrogen with de-gassed brine (ca. 450 mL), dried (Na2SO4) under nitrogen and concentrated in vacuo to give the crude title compound (16 g) as an air-sensitive orange oil.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 24 h
  4. customquenched with de-gassed saturated aqueous sodium bicarbonate (450 mL)
  5. extractionextracted under nitrogen with de-gassed methylene chloride (3×ca. 150 mL)
  6. washThe combined extracts were washed under nitrogen with de-gassed brine (ca. 450 mL)
  7. dry with materialdried (Na2SO4) under nitrogen
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6047823fe5b4c1097cfc68448a38596
Source dataset
uspto-grants-2010_04
Patent number
US07696221B2

Reaction notes

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