Diisopropylethylamine → HCID 66744764, compound

HRID 708910Notes

Reaction equation

HRID 708910 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][NH:12][CH3:13].[CH2:14]([O:21][C:22]([O:24]N1C(=O)CCC1=O)=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][N:12]([CH3:13])[C:22](=[O:24])[O:21][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 59315032HCID 59315032, compound

Product 1

HCID 66744764HCID 66744764, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1-(2-bromo-5-nitrophenyl)-N-methylmethanamine (7 g, 28.6 mmol, see WO 2008/079836 for preparation) in DMF (30 ml), was added N-(benzyloxycarbonyloxy) succinimide (8.54 g, 34.3 mmol) and N,N-diisopropylethylamine (9.98 ml, 57.1 mmol). The mixture was stirred rt for 1 h, then quenched with water, extracted with EtOAc (3×30 ml). The organic layer was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0-60% EtOAc in hexane) to yield 36A (10.66 g, 28.1 mmol, 98% yield). MS (ESI) m/z: 379.2 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ ppm 7.92-8.02 (m, 2H) 7.74 (d, J=6.15 Hz, 1H) 7.33-7.42 (m, 2H) 7.28 (s, 3H) 5.22 (s, 1H) 5.15 (s, 1H) 4.61 (d, J=18.46 Hz, 2H) 3.02 (s, 3H).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc (3×30 ml)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0-60% EtOAc in hexane)

Sources & evidence

ORD record
ord-fd021841fec24a218c10076b156ad69d
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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