Benzyl Bromide → HCID 91009143, compound

HRID 857372Notes

Reaction equation

HRID 857372 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([CH:18]([CH3:20])[CH3:19])=[CH:13][C:14]([OH:17])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([CH:18]([CH3:19])[CH3:20])=[CH:13][C:14]([O:17][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 91416132HCID 91416132, compound

Product 1

HCID 91009143HCID 91009143, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the compound of Step 3 (130 mg, 0.45 mmol) in DMF (2 mL) at 0° C., was added benzyl bromide (100 mL) and Cs2CO3 (300 mg, 0.92 mmol). The reaction mixture was warmed to r.t for 1 hour. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to give the title compound (130 mg).

Workup

  1. temperatureThe reaction mixture was warmed
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-eff6685b24af4eefa5cd3692e6053cf4
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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