Sodium Carbonate → Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

HRID 2220370Notes

Reaction equation

HRID 2220370 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH:13]([CH3:15])[CH3:14])[CH:3]=1.[CH2:16]([N:23]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([N:23]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH:13]([CH3:15])[CH3:14])[CH:3]=2)=[CH:28][CH:27]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 22171360(4-[2-[Benzyl(tert-butoxycarbonyl)amino]ethyl]phenyl]boronic acidHCID 24824349Methyl 4-bromo-2-(isopropylamino)benzoate

Product 1

HCID 69102971Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylateYield 96%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-bromo-2-(isopropylamino)benzoate (433 mg) in 1,2-dimethoxyethane (6.5 ml) were added [4-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]phenyl]boronic acid (848 mg), tetrakis(triphenylphosphine)palladium (184 mg) and aqueous solution of sodium carbonate (2M, 3.5 ml), and the mixture was stirred at 70° C. for 2 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=17/3) to give methyl 4′-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-3-(isopropylamino)-4-biphenylcarboxylate (768 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=17/3)

Sources & evidence

ORD record
ord-2ac86cdc741241a18611cd06c5397a94
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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