5-Aminoisoquinoline → HCID 89499916, compound

HRID 1467805Notes

Reaction equation

HRID 1467805 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].CC([O-])(C)C.[K+]>C1COCC1>[CH:1]1[C:10]2[C:5](=[C:6]([N:11]3[CH2:13][CH2:14][CH2:15][CH2:16][C:17]3=[O:18])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 707665-AminoisoquinolineHCID 5211735-Bromovaleryl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 89499916HCID 89499916, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To isoquinolin-5-amine (0.24 g, 1.665 mmol) in THF (5 mL) was added 5-bromopentanoyl chloride (0.223 mL, 1.665 mmol) followed by addition of THF (3 mL). The reaction was cooled with ice bath and to the above solution was added 1M KOtBu in THF (3.66 mL, 3.66 mmol). After 24 h, the reaction was quenched with H2O (10 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (10 mL) and dried (MgSO4) to afford 0.4 g of 33A as a dark solid. MS (ESI) m/z: 227 (M+H)+.

Workup

  1. temperatureThe reaction was cooled with ice bath and to the above solution
  2. customthe reaction was quenched with H2O (10 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-cb1f51642a6444b58e5402803255b196
Source dataset
uspto-grants-2015_04
Patent number
US09000172B2

Reaction notes

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