1-Chloro-4-(chloromethyl)benzene → HCID 11654892, compound

HRID 1988836Notes

Reaction equation

HRID 1988836 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[C:14]([CH3:18])=[C:15]([CH3:17])[NH:16][C:9]=23)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[Cl:45][C:46]1[CH:53]=[CH:52][C:49]([CH2:50]Cl)=[CH:48][CH:47]=1>O1CCCC1>[ClH:45].[Cl:45][C:46]1[CH:53]=[CH:52][C:49]([CH2:50][N:16]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][C:8]=3[O:7][CH2:6][C:5]3[CH:19]=[CH:20][C:2]([F:1])=[CH:3][CH:4]=3)[C:14]([CH3:18])=[C:15]2[CH3:17])=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 687053187-[(4-Fluorophenyl)methoxy]-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 11654892HCID 11654892, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(4-fluorobenzyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (25 mg, 0.105 mmol) prepared in Step 1, potassium tert-butoxide (13.6 mg, 0.163 mmol), and a catalytic amount of 18-crown-6 were added to anhydrous tetrahydrofuran (2 ml). 4-Chlorobenzyl chloride (0.089 ml, 0.160 mmol) was added to the reaction mixture, which was then stirred for 12 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/methylene chloride/methanol=10/10/1, (v/v/v)), dissolved in ethyl acetate (1 ml), and then saturated with hydrochloric acid gas. The resulting precipitate was filtered to give the titled compound as a white solid (6.9 mg, 15.8%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/methylene chloride/methanol=10/10/1, (v/v/v))
  3. dissolutiondissolved in ethyl acetate (1 ml)
  4. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-e78ad4a6295c4e9f8689bcd88ec3213a
Source dataset
uspto-grants-2010_01
Patent number
US07642269B2

Reaction notes

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