Allyl iodide → HCID 57941439, compound

HRID 1437923Notes

Reaction equation

HRID 1437923 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.[CH2:22](I)[CH:23]=[CH2:24]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[CH2:24]([N:9]1[C:10]2[C@@:11]3([CH3:21])[C:18]([CH3:20])([CH3:19])[C@H:14]([CH2:13][CH2:12]3)[C:15]=2[C:16](=[O:17])[N:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH:23]=[CH2:22]

Participants

5

Reactant 2

HCID 11166Allyl iodideHCID 57941332HCID 57941332, compound2×

Product 1

HCID 57941439HCID 57941439, compoundYield 33%

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 allyl iodide (100 μL, 1.1 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 to give (4S,7R)-1-allyl-2-(2-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (56 mg, 33%) as an orange solid. ES(+)-MS (M+H) 327.

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

Sources & evidence

ORD record
ord-1f437a8ada75450182622b74e56c4b2f
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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