Benzyl Bromide → HCID 21056496, compound

HRID 2215863Notes

Reaction equation

HRID 2215863 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][C:5]=1[N+:18]([O-])=O.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][C:5]=1[NH2:18]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 69034741HCID 69034741, compound

Product 1

HCID 21056496HCID 21056496, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of CsCO3 (4.9 g, 15 mmoles) and (4-tert-Butoxycarbonylamino-2-nitro-benzoic acid methyl ester (2.96 g, 10 mmoles) in anhydrous DMF (100 mL) was added benzyl bromide (2.57 g, 15 mmoles) and the resulting mixture was stirred at room temperature for 12 hrs. The reaction mixture was filtered, concentrated, diluted with ethyl acetate, and washed with 5% citric acid, saturated NaHCO3 solution and water. The organic phase was hydrogenated over 10% Pd/C in EtOAc. After 12 hr, the mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to give a crude oil which was purified by column chromatography to furnish the desired product as an off-white solid (2.05 g, 57% yield). ES+ MS showed 357 m/z, the correct mass for the product. 1H NMR (400 MHz, DMSO-d6) showed β=1.34 (s, 9H), 3.71 (s, 3H), 4.74 (s, 2H), 6.39 (d, J=9 Hz, 1H), 6.62 (s, 1+2H), 7.19 (d, J=7 Hz, 2H), 7.24 (d, J=7 Hz, 1H), 7.32 (dd, J1=J2=7 Hz, 2H),.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with 5% citric acid, saturated NaHCO3 solution and water
  5. waitAfter 12 hr
  6. filtrationthe mixture was filtered through a celite pad
  7. concentrationthe filtrate was concentrated in vacuo
  8. customto give a crude oil which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-602542bea0f245588017a8aa23f59d4c
Source dataset
uspto-grants-2006_09
Patent number
US07109332B2

Reaction notes

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