3-Fluorobenzyl chloride → 1-(3-fluorobenzyl)-2,3-dimethyl-7-(4-vinylphenyl)-1H-pyrrolo[2,3-c]pyridine hydrochloride

HRID 1932349Notes

Reaction equation

HRID 1932349 reaction equation
C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].[CH3:25][C:26]1[NH:42][C:29]2=[C:30]([C:34]3[CH:39]=[CH:38][C:37]([CH:40]=[CH2:41])=[CH:36][CH:35]=3)[N:31]=[CH:32][CH:33]=[C:28]2[C:27]=1[CH3:43].[F:44][C:45]1[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=1)[CH2:48][Cl:49]>O1CCCC1>[ClH:49].[F:44][C:45]1[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=1)[CH2:48][N:42]1[C:29]2=[C:30]([C:34]3[CH:39]=[CH:38][C:37]([CH:40]=[CH2:41])=[CH:36][CH:35]=3)[N:31]=[CH:32][CH:33]=[C:28]2[C:27]([CH3:43])=[C:26]1[CH3:25]

Participants

6

Reactant 4

HCID 99743-Fluorobenzyl chlorideHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 671415892,3-dimethyl-7-(4-vinylphenyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 671428601-(3-fluorobenzyl)-2,3-dimethyl-7-(4-vinylphenyl)-1H-pyrrolo[2,3-c]pyridine hydrochlorideYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18-Crown-6 (2.5 mg, 0.0097 mmol) and potassium tert-butoxide (33 mg, 0.291 mmol) were added to a solution of 2,3-dimethyl-7-(4-vinylphenyl)-1H-pyrrolo[2,3-c]pyridine (24 mg, 0.097 mmol) prepared in Example 242 in anhydrous tetrahydrofuran (0.5 ml). The reaction mixture was stirred for 30 minutes at room temperature and 3-fluorobenzyl chloride (20 μl, 0.16 mmol) was added thereto. The reaction mixture was stirred overnight and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography. The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 3.8 mg of the titled compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-01e2402302b5469084bfb478fc740561
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

Loading…