Phenethyl bromide → HCID 21904372, compound

HRID 479841Notes

Reaction equation

HRID 479841 reaction equation
[C:1]([CH:11]([CH:27]1[NH:32][CH2:31][CH2:30][NH:29][CH2:28]1)[N:12]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[C:13]([CH:15]1[CH2:18][CH2:17][CH2:16]1)=[O:14])(OCC1C=CC=CC=1)=O.C(Br)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])([O-])=O.[K+].[K+]>CO.CC#N.[Pd]>[CH2:1]([CH:11]([CH:27]1[NH:32][CH2:31][CH2:30][NH:29][CH2:28]1)[N:12]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[C:13]([CH:15]1[CH2:18][CH2:17][CH2:16]1)=[O:14])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 21904434HCID 21904434, compound

Product 1

HCID 21904372HCID 21904372, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 213 (0.302 mmol, 127 mg) in CH3OH (1 mL) at 25° C. was treated with 30% Pd-C (25 mg) and then placed under a hydrogen atmosphere. The reaction mixture stirred for 12 h and then was filtered through a pad of celite. The solvents were removed in vacuo and the resulting oil was then treated with phenethyl bromide (1.5, equiv, 0.453 mmol, 62 μL) and K2CO3 (2.0 equiv, 0.604 mmol, 83 mg) in CH3CN (1.0 mL). The reaction mixture stirred for 12 h at 65° C. The reaction mixture was then purified directly by chromatography (PTLC, SiO2, 20 cm×20 cm, 1 mm, EtOAc-10% CH3OH) which provided 214 (51 mg, 118 mg theoretical, 43%) as colorless oil: Rf 0.45 (SiO2, EtOAc-10% CH3OH); LRMS m/z 390 (M+, C26H34N2O, requires 390).

Workup

  1. filtrationwas filtered through a pad of celite
  2. customThe solvents were removed in vacuo
  3. stirringThe reaction mixture stirred for 12 h at 65° C
  4. customThe reaction mixture was then purified directly by chromatography (PTLC, SiO2, 20 cm×20 cm, 1 mm, EtOAc-10% CH3OH) which

Sources & evidence

ORD record
ord-238f217c81104e8fb5609ab0c7047ed2
Source dataset
uspto-grants-2003_11
Patent number
US06645980B1

Reaction notes

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