Benzyl Bromide → HCID 67141681, compound

HRID 1932354Notes

Reaction equation

HRID 1932354 reaction equation
C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:33]=[CH:34][CH:35]=[C:36]3[C:40]([CH2:41][O:42][CH2:43][CH3:44])=[C:39]([CH3:45])[NH:38][C:37]=23)=[CH:28][CH:27]=1.[CH2:46](Br)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>O1CCCC1>[ClH:25].[CH2:46]([N:38]1[C:37]2=[C:32]([C:29]3[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][CH:30]=3)[N:33]=[CH:34][CH:35]=[C:36]2[C:40]([CH2:41][O:42][CH2:43][CH3:44])=[C:39]1[CH3:45])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 67141977HCID 67141977, compound

Product 1

HCID 67141681HCID 67141681, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18-Crown-6 (2 mg, 0.006 mmol) and potassium tert-butoxide (7 mg, 0.066 mmol) were added to a solution of 7-(4-chlorophenyl)-3-ethoxymethyl-2-methyl-1H-pyrrolo[2,3-c]pyridine (20 mg, 0.066 mmol) prepared in Example 466 in anhydrous tetrahydrofuran (1 ml). The reaction mixture was stirred for 30 minutes at room temperature and then benzyl bromide (11.8 μl, 0.099 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 (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 10 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 (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-af525cb17d2947b7a6a11ee676add41b
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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