4-Toluenesulfonyl chloride → tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylate

HRID 268713Notes

Reaction equation

HRID 268713 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([NH2:19])=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]#[N:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68966998tert-Butyl 5-carbamoylisoindoline-2-carboxylate

Product 1

HCID 18630967tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylateYield 490.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of N-t-butoxycarbonyl-5-aminocarbonylisoindoline (D14) (140 mg) in pyridine (3 ml) at rt was treated with 4-toluenesulfonyl chloride (305 mg) and then stirred overnight. Following evaporation the residue was dissolved in EtOAc (10 ml), washed with saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml), dried (MgSO4) and concentrated. The residue was chromatographed on a silica gel flash column [step gradient 5-20% EtOAc in light petroleum 40-60] to give the title compound (D15) (0.64 g). MS electrospray (+ion) 189 (MH+-t-Bu). 1H NMR δ (CDCl3): 7.56 (2H, m), 7.38 (1H, m), 4.71 (4H, m), 1.52 (9H, s).

Workup

  1. customevaporation the residue
  2. dissolutionwas dissolved in EtOAc (10 ml)
  3. washwashed with saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel flash column [step gradient 5-20% EtOAc in light petroleum 40-60]

Sources & evidence

ORD record
ord-9b4202ec21a3459294d6ce7c5f5f88a7
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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