N-methyl-2-pyrrolidone → HCID 86687438, compound

HRID 1473395Notes

Reaction equation

HRID 1473395 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH:13]=[C:12]2Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu][C:22]#[N:23].CN1C(=O)CCC1>C(OCC)(=O)C>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH:13]=[C:12]2[C:22]#[N:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 86687439HCID 86687439, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86687438HCID 86687438, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A vial was charged with 6-(benzylthio)-4-bromoisoquinolin-1(2H)-one (0.583 g, 1.684 mmol), copper (i) cyanide (0.052 ml, 1.684 mmol), and NMP (8.42 ml). The reaction was heated to 200° C. and stirred for four hours. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (40 g silica gel column, gradient elution 0 to 10% MeOH:EtOAc) to afford 6-(benzylthio)-1-oxo-1,2-dihydroisoquinoline-4-carbonitrile as a brown solid. m/z (ESI) 293.1 (M+H)+.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified via column chromatography (40 g silica gel column, gradient elution 0 to 10% MeOH:EtOAc)

Sources & evidence

ORD record
ord-1f9fcce285084d63827c22353b1092c1
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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