m,alpha-Dichlorotoluene → HCID 67141247, compound

HRID 1932404Notes

Reaction equation

HRID 1932404 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[NH:34][C:11]2=[C:12]([N:24]3[CH2:33][CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25]3)[N:13]=[C:14]([CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[CH:15]=[C:10]2[C:9]=1[CH3:35].C1OCCOCCOCCOCCOCCOC1.[Cl:54][C:55]1[CH:56]=[C:57]([CH:60]=[CH:61][CH:62]=1)[CH2:58]Cl>O1CCCC1>[ClH:54].[Cl:54][C:55]1[CH:56]=[C:57]([CH:60]=[CH:61][CH:62]=1)[CH2:58][N:34]1[C:11]2=[C:12]([N:24]3[CH2:33][CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25]3)[N:13]=[C:14]([CH2:16][N:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)[CH:15]=[C:10]2[C:9]([CH3:35])=[C:8]1[CH3:7]

Participants

6

Reactant 4

HCID 12103m,alpha-DichlorotolueneHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 67142308HCID 67142308, compound

Product 1

HCID 67141247HCID 67141247, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (15 mg, 0.12 mmol) was added to a solution of 2-[2,3-dimethyl-5-(4-methylpiperazin-1-ylmethyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,2,3,4-tetrahydroisoquinoline (30 mg, 0.074 mmol) prepared in Step 1 of Example 874 and 18-crown-6 (3.1 mg, 0.012 mmol) in anhydrous tetrahydrofuran (2 ml). The reaction mixture was stirred for 1 hour at room temperature and then 3-chlorobenzyl chloride (15.2 μl, 0.12 mmol) was added thereto. The reaction mixture was stirred overnight at room temperature and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 21.0 mg of the titled compound as a white solid.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5
  4. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  5. filtrationfiltered

Sources & evidence

ORD record
ord-b23cac4fdcf14b8195061d4245e79235
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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