Ethyl cyanoacetate → HCID 68711116, compound

HRID 222120Notes

Reaction equation

HRID 222120 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].Br.Br[CH:11]1[CH2:20][CH2:19][C:18]2[CH:17]=[N:16][CH:15]=[CH:14][C:13]=2[C:12]1=[O:21].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:7]([O:6][C:4](=[O:5])[CH:3]([C:1]#[N:2])[CH:11]1[CH2:20][CH2:19][C:18]2[CH:17]=[N:16][CH:15]=[CH:14][C:13]=2[C:12]1=[O:21])[CH3:8]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 81531DiisopropylethylamineHCID 68707913HCID 68707913, compound

Product 1

HCID 68711116HCID 68711116, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, cold (4° C.) solution of ethyl cyanoacetate (52.2 mmol) and 6-bromo-7,8-dihydro-6H-isoquinolin-5-one 8B (6.5 mmol) in DMF (10 mL), DIEA (19.5 mmol) was added. The mixture was brought to rt and stirred for 4 h. Solvent was removed and the residue, dissolved in DCM, was repeatedly washed with water. The organic layer was dried (Na2SO4) and concentrated. Purification by chromatography on silica gel (DCM/MeOH 98:2) provided the title compound in 95% yield. ESI (+) MS: m/z 259 (MH+). 1H NMR: 1.15-1.32 (m, 3H), 1.98-2.44 (m, 2H), 3.59-3.82 (m, 3H), 4.20-4.28 (m, 2H), 4.70 (s, 1H), 7.67-7.73 (m, 1H), 8.64-8.68 (m, 1H), 8.75-8.78 (m, 1H).

Workup

  1. customwas brought to rt
  2. customSolvent was removed
  3. dissolutionthe residue, dissolved in DCM
  4. washwas repeatedly washed with water
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by chromatography on silica gel (DCM/MeOH 98:2)

Sources & evidence

ORD record
ord-e078658cc96b4a72a934df28029c8cb9
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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