Hydrochloric Acid → 5-bromo-6-cyclopropyl-1H-pyrrolo[2,3-b]pyridine

HRID 531448Notes

Reaction equation

HRID 531448 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:13]=[C:12]([Si](C)(C)C)[NH:11][C:5]2=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.Cl.[OH-].[Na+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH:13]=[CH:12][NH:11][C:5]2=[N:6][C:7]=1[CH:8]1[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 900315195-bromo-6-cyclopropyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 900648045-bromo-6-cyclopropyl-1H-pyrrolo[2,3-b]pyridineYield 79.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A stirred solution of 5-bromo-6-cyclopropyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.5 g, 4.84 mmol), tert-butanol (15 mL), 9N-hydrochloric acid (15 mL) was heated to reflux for 8 hours. Reaction mixture was cooled and basified with 50% sodium hydroxide to pH 8, extracted with ethyl acetate. Organic portion was in turn washed with brine, dried over sodium sulfate and concentrated to give 910 mg (79.13% yield) of the title compound. 1H NMR (CDCl3, 300 MHz) δ 9.43 (bs, 1H), 8.06 (s, 1H), 6.39-6.38 (m, 1H), 2.647-2.603 (m, 1H), 1.09-1 (m, 4H). LCMS: m/z=237.0 (M+1).

Workup

  1. temperatureto reflux for 8 hours
  2. customReaction mixture
  3. temperaturewas cooled
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d3e8c8807694b2ebc0eb8e0bbc68cd3
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…