Sulfuric Acid → 5-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine

HRID 2375942Notes

Reaction equation

HRID 2375942 reaction equation
[Br:1][C:2]1[C:3]([Cl:21])=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.OS(O)(=O)=O>CC(O)C>[Br:1][C:2]1[C:3]([Cl:21])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 575376865-Bromo-4-chloro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 457897885-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 5-bromo-4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (10.1 g, ≈14.0 mmol; crude material prepared according to Tetrahedron Lett., 2004, 45, 2317-2319) in IPA (250 mL) at 0° C. was added 2N H2SO4 (25 mL) and the mixture was allowed to warm to RT and stirred overnight. IPA was evaporated at 35° C. and water was added to the residue and neutralized with 2N NaOH. The precipitate formed was filtered, washed with water followed by hexane, and dried under vacuum to yield the title compound as off-white solid. MS (ES+): m/z 233.01 (100) [MH+]; HPLC: tR=4.51 min (ZQ2000, polar—15 min).

Workup

  1. customIPA was evaporated at 35° C.
  2. additionwater was added to the residue
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c228795e083445bbbf68ba065b06907c
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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