Isopropyl iodide → HCID 16118897, compound

HRID 1437924Notes

Reaction equation

HRID 1437924 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C@@H:14]3[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]3)[C:10]=2[NH:9]1.I[CH:23]([CH3:25])[CH3:24]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C@@H:14]3[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]3)[C:10]=2[N:9]1[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 6362Isopropyl iodideHCID 57941332HCID 57941332, compound2×

Product 1

HCID 16118897HCID 16118897, compoundYield 4.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of a (4S,7R)-2-(2-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 12; 150 mg, 0.52 mmol) and 2-iodopropane (105 μL, 1.05 mmol) in N,N-dimethylformamide (2 mL) in a microwave reaction tube was heated to 100° C. and stirred for 18 h. The reaction mixture was allowed to cool, diluted with saturated sodium bicarbonate, and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified using an ISCO CombiFlash® Sg100c chromatography system with an Isco 12 g column, eluting with 25-100% ethyl acetate/hexanes followed by crystallization from dichloromethane to give (4S,7R)-2-(2-fluoro-phenyl)-1-isopropyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (7 mg, 4%) as an yellow solid. ES(+)-MS (M+H) 329.

Workup

  1. customin a microwave reaction tube
  2. temperatureto cool
  3. extractionextracted twice with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified
  9. washeluting with 25-100% ethyl acetate/hexanes
  10. customfollowed by crystallization from dichloromethane

Sources & evidence

ORD record
ord-ea102389e26e48978e0d1765a8ac6ed9
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

Loading…