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

HRID 1932370Notes

Reaction equation

HRID 1932370 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-methyl sulfanyl-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-b9b62d0520a14644953f6a866fc6a49a
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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