Ethyl Bromide → HCID 11596318, compound

HRID 13000Notes

Reaction equation

HRID 13000 reaction equation
Br[CH2:2][CH3:3].[C:4]([O:8][C:9](=[O:30])[NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][C:16]1[C:17]2[C:22]([CH:23]=[C:24]3[C:29]=1[CH:28]=[CH:27][CH:26]=[CH:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH3:7])([CH3:6])[CH3:5].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:4]([O:8][C:9](=[O:30])[NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:15][C:16]1[C:17]2[C:22]([CH:23]=[C:24]3[C:29]=1[CH:28]=[CH:27][CH:26]=[CH:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:2][CH3:3])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 11682094{3-[(Anthracen-9-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 11596318HCID 11596318, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

Bromoethane (489 mg, 4.48 mmol) was dissolved in anhydrous acetonitrile and was added to the stirring mixture of compound 12a (545 mg, 1.5 mmol) and anhydrous K2CO3 (620 mg, 4.48 mmol). The mixture was then stirred at 75° C. under a N2 atmosphere overnight. After the confirmation of the disappearance of the 12a by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 12b as a light yellow oil. Yield 80%; Rf=0.35 (3% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.39 (d, 2H), 8.30 (s, 1H), 7.90 (d, 2H), 7.40 (m, 4H), 4.54 (br t, 1H), 4.37 (s, 2H), 2.74 (q, 2H), 2.60 (q, 2H), 2.39 (t, 2H), 1.44 (q, 2H), 1.31 (m, 9H), 1.12 (t, 3H); 13C NMR (CDCl3) δ 155.7, 131.3 (2C), 131.2 (2C), 130.4 (2C), 129.0 (2C), 127.5 (2C), 125.7 (2C), 124.8 (2C), 78.3, 50.6, 50.5, 47.7, 39.1, 28.6 (3C), 26.6, 11.8. HRMS (FAB) m/z calcd. for C25H32N2O2 (M+H)+ 393.2537; found 393.2523.

Workup

  1. concentrationAfter the confirmation of the disappearance of the 12a by TLC, the solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. washwashed three times with aqueous sodium carbonate
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0aae9ffd26c842df9d618b60b034bbcd
Source dataset
uspto-grants-2010_06
Patent number
US07728041B2

Reaction notes

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