1,2,3,4-Tetrahydroisoquinoline → HCID 67142286, compound

HRID 1445084Notes

Reaction equation

HRID 1445084 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([S:11][CH3:12])=[C:9]([CH3:13])[NH:8][C:7]=12.[CH2:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][NH:15]1>>[CH3:13][C:9]1[NH:8][C:7]2=[C:2]([N:15]3[CH2:16][CH2:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:14]3)[N:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[S:11][CH3:12]

Participants

3

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 3531131HCID 3531131, compound

Product 1

HCID 67142286HCID 67142286, compound

Conditions

Temperature
140 °C

Procedure

7-Chloro-2-methyl-3-methylsulfanyl-1H-pyrrolo[2,3-c]pyridine (418 mg) prepared in Step 1 was added to 1,2,3,4-tetrahydroisoquinoline (3 ml). The reaction mixture was stirred overnight at 140° C., cooled to room temperature, and then purified with silica gel column chromatography to give 440 mg of the titled compound as pale yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. custompurified with silica gel column chromatography

Sources & evidence

ORD record
ord-61bfb741f8c04aa1aa808a942d4c3782
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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