HCID 58149918, compound → HCID 58149902, compound

HRID 2192498Notes

Reaction equation

HRID 2192498 reaction equation
Br[Zn][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].Br[C:12]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([C:22]#[N:23])[C:16]=2[CH:15]=[CH:14][N:13]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[CH:15]=[CH:14][N:13]=[C:12]2[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:23]

Participants

5

Reactant 2

HCID 58149918HCID 58149918, compoundHCID 178471551HCID 178471551, compound

Product 1

HCID 58149902HCID 58149902, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Bromo[4-(ethyloxy)-4-oxobutyl]zinc (0.5 M in THF, 26 ml) was added dropwise to a solution of 1-bromo-5-isoquinolinecarbonitrile (D38; 1 g) and tetrakis(triphenylphosphine)palladium(0) (20 mg) in THF (5 ml). The resulting solution was heated to reflux for 3 hours. The solvent was evaporated in vacuo and the residue was dissolved in DCM (50 ml). The organic solution was washed with 0.5 M aq. NaOH (15 ml), followed by washing with water and brine. The organic phase was dried over anhydrous sodium sulphate. The dried solution was filtered and the filtrate was concentrated. The residue was purified by column chromatography to give the title compound (0.65 g). δH (CDCl3, 400 MHz): 1.28 (3H, t), 2.20 (2H, m), 2.50 (2H, m), 3.41 (2H, m), 4.16 (2H, q), 7.71 (1H, dd), 7.93 (1H, d), 8.12 (1H, dd), 8.54 (1H, d), 8.63 (1H, d). MS (ES): C16H16N2O2 requires 268. found 269.1 (M+H+).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe residue was dissolved in DCM (50 ml)
  5. washThe organic solution was washed with 0.5 M aq. NaOH (15 ml)
  6. washby washing with water and brine
  7. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  8. filtrationThe dried solution was filtered
  9. concentrationthe filtrate was concentrated
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-358e93d8f00c423d9ea963fd52ca2ee9
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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