2-(Bromomethyl)-5-(trifluoromethyl)furan → HCID 57941315, compound

HRID 1437950Notes

Reaction equation

HRID 1437950 reaction equation
[CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.Br[CH2:17][C:18]1[O:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=1>CN(C)C=O>[CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:12])([CH3:13])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[N:3]1[CH2:17][C:18]1[O:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 57941341HCID 57941341, compound2×

Product 1

HCID 57941315HCID 57941315, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and 2-bromomethyl-5-trifluoromethyl-furan (144 mg, 0.63 mmol) in N,N-dimethylformamide (5 mL) was heated at 110° C. for 2 days. The reaction mixture was evaporated and the residue was dissolved in ethyl acetate (50 mL), washed with water (2×25 mL) and brine (25 mL), dried (magnesium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 2-3% methanol/dichloromethane to give (4S,7R)-1,7,8,8-tetramethyl-2-(5-trifluoromethyl-furan-2-ylmethyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (136 mg, 78%) as a white solid. APCI-MS (M+H) 355.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with water (2×25 mL) and brine (25 mL)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by flash chromatography
  8. washeluting with 2-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-3900007144b449a08c3cb7140c8fd0d4
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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