HCID 58149871, compound → HCID 58149913, compound

HRID 2192497Notes

Reaction equation

HRID 2192497 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[C:16](=[C:17]([C:22]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH:34]([CH3:36])[CH3:35])=[C:29]([Cl:37])[CH:28]=4)[O:24][N:23]=3)[CH:18]=[CH:19][CH:20]=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>[Cl:37][C:29]1[CH:28]=[C:27]([C:25]2[O:24][N:23]=[C:22]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:16]=3[CH:15]=[CH:14][N:13]=[C:12]4[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:26]=2)[CH:32]=[CH:31][C:30]=1[O:33][CH:34]([CH3:36])[CH3:35]

Participants

5

Reactant 2

HCID 58149871HCID 58149871, compoundHCID 178471551HCID 178471551, compound

Product 1

HCID 58149913HCID 58149913, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Bromo[4-(ethyloxy)-4-oxobutyl]zinc (Aldrich; 0.5 M in THF, 2 ml) was added dropwise to a solution of 1-bromo-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline (D40; 0.15 g) and tetrakis(triphenylphosphine)palladium(0) (50 mg) in THF (5 ml). The resulting solution was heated to reflux for 1 hour. The solvent was evaporated in vacuo and the residue was dissolved in DCM (20 ml). The organic solution was washed with 0.5 M aq. NaOH (8 ml), then 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 (0.1 g).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 1 hour
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe residue was dissolved in DCM (20 ml)
  5. washThe organic solution was washed with 0.5 M aq. NaOH (8 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationThe dried solution was filtered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e0dd0e9b0b6649a6bb6c8791c13827dc
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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