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Iodoethane → HCID 69018701, compound

HRID 1437918
Notes
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Reaction equation

HRID 1437918 reaction equation
I[CH2:2][CH3:3].[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:19](=[O:20])[C:18]2[C@@H:17]3[C:21]([CH3:23])([CH3:22])[C@@:14]([CH3:24])([CH2:15][CH2:16]3)[C:13]=2[NH:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:19]([O:20][CH2:2][CH3:3])=[C:18]2[C:13]([C:14]3([CH3:24])[C:21]([CH3:23])([CH3:22])[CH:17]2[CH2:16][CH2:15]3)=[N:12]1.[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:19](=[O:20])[C:18]2[C@@H:17]3[C:21]([CH3:23])([CH3:22])[C@@:14]([CH3:24])([CH2:15][CH2:16]3)[C:13]=2[N:12]1[CH2:2][CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 57941362HCID 57941362, compound2×

Product 2

HCID 57941485HCID 57941485, compoundYield 9%HCID 69018701HCID 69018701, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

Iodoethane (14 μL, 0.18 mmol) was added to (4S,7R)-2-(2-chloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 10; 47 mg, 0.16 mmol) and potassium carbonate (43 mg, 0.31 mmol) in dimethylformamide (1 mL). The mixture was heated at 60 degrees for 4 h, and then stirred at room temperature over the weekend. The reaction mixture was diluted with ethyl acetate and washed with NaOH. The solvent was evaporated from the ethyl acetate layer and the residue was purified by flash chromatography, eluting with 0-70% ethyl acetate/hexanes, to give 2-(2-chloro-phenyl)-3-ethoxy-7,8,8-trimethyl-4,5,6,7-tetrahydro-2H-4,7-methano-indazole (12.3 mg, 16%) and (4S,7R)-2-(2-chloro-phenyl)-1-ethyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (4.4 mg, 9%). APCI-MS (M+H) 331.

Workup

  1. temperatureThe mixture was heated at 60 degrees for 4 h
  2. washwashed with NaOH
  3. customThe solvent was evaporated from the ethyl acetate layer
  4. customthe residue was purified by flash chromatography
  5. washeluting with 0-70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c57f712bcfe3441383c43008e880fdf5
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07622492B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes