6-Bromoisoquinoline → Isoquinoline-6-carbonitrile

HRID 598820

Reaction equation

HRID 598820 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[C:12]([Cu])#[N:13]>CN1C(=O)CCC1>[CH:8]1[C:9]2[C:4](=[CH:3][C:2]([C:12]#[N:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 3136816-BromoisoquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 23130705Isoquinoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

6-Bromoisoquinoline (0.876 g, 4.18 mmol) purchased from Gateway Chemical Technology, Inc. was mixed with CuCN (1.12 g, 12.54 mmol) in 5 mL NMP in a microwave heating tube. The tube was heated under microwave to 150° C. for 1 hour and 170° C. for one hour. The reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3. After removing the solvent, the remaining residue was passed through a silica gel plug using 5% 2M ammonia in MeOH in DCM as the eluant. The crude product (100 mg) was used directly in the next step.

Workup

  1. temperatureheating tube
  2. customThe reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  3. customAfter removing the solvent

Sources & evidence

ORD record
ord-08e90cabb20848959ae7c039aa310e8a
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Linked notes

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