Potassium Carbonate → HCID 16040141, compound

HRID 252068Notes

Reaction equation

HRID 252068 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[CH3:10][C:11]1[CH:12]=[C:13]([CH2:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:14]=[C:15]2[C:19]=1[C:18](=[O:20])[N:17]([CH2:21][CH:22]([CH:24]1CCCC[CH2:25]1)C)[CH2:16]2.C(=O)([O-])[O-].[K+].[K+].CC(C)([O-])C.[Na+]>O.C(#N)C>[CH:22]1([CH2:21][N:17]2[CH2:16][C:15]3[C:19](=[C:11]([CH3:10])[CH:12]=[C:13]([CH2:30][CH:31]4[CH2:32][CH2:33][N:34]([CH2:4][C:3]5[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=5[F:1])[CH2:35][CH2:36]4)[CH:14]=3)[C:18]2=[O:20])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 23676156Sodium t-butoxideHCID 66872616HCID 66872616, compound

Product 1

HCID 16040141HCID 16040141, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-Fluorobenzyl bromide (47 μL, 0.377 mmol), 7-methyl-5-piperidin-4-ylmethyl-2-cyclohexylpropyl-2,3-dihydro-isoindol-1-one (75 mg, 0.251 mmol) and potassium carbonate (104 mg, 0.753 mmol) was added acetonitrile (3.0 mL). The mixture was stirred at 80° C. for 4 hours. 1 scoop of Sodium tert-butoxide (˜200 mg) was added and stirring continued overnight at 80° C. The mixture was cooled to room temperature, water (2.0 mL) was added and the product was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. Column chromatography provided the title compound as a yellow oil (6.6 mg, 6%). 1H NMR (300 MHz, CDCl3): δ 7.38 (m, 1H), 7.23-7.13 (m, 1H), 7.11-7.00 (m, 3H), 6.96 (s, 1H), 4.41 (s, 2H), 3.61 (s, 2H), 3.46-3.44 (d, 2H), 2.95-2.92 (d, 2H), 2.70 (s, 3H), 2.59-2.57 (d, 2H), 2.01-1.98 (t, 2H), 1.65-1.61 (m, 3H), 1.38-1.27 (m, 2H), 1.04 (m, 1H), 0.60-0.55 (m, 2H), 0.36-0.32 (m, 2H).

Workup

  1. stirringstirring continued overnight at 80° C
  2. temperatureThe mixture was cooled to room temperature
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a4c1b64a87294cc9a94dc6c246b6c583
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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