Hydrochloric Acid → 5-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1994189Notes

Reaction equation

HRID 1994189 reaction equation
C([Si](C)(C)[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]2[CH:8]=[CH:7]1)(C)(C)C.Cl>CO>[CH3:15][C:13]1[CH:14]=[C:9]2[CH:8]=[CH:7][NH:6][C:10]2=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 575978501-(tert-Butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 205974295-methyl-1H-pyrrolo[2,3-b]pyridineYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of the crude azaindole 8 (0.64 mmol) in MeOH (6 mL) was added a 10% solution of HCl in methanol (3 mL). After 20 min the mixture was concentrated and partitioned between AcOEt and saturated aqueous NaHCO3 solution. The aqueous layer was extracted with AcOEt (2×) and the combined organic solutions were dried (MgSO4), filtered and concentrated. The residue was purified by PTLC using 5% MeOH in CH2Cl2 to afford the desired methyl derivative 9 (68 mg, 81% over 3 steps). 1H NMR (400 MHz; CDCl3) δ 2.45 (s, 3H), 6.42 (d, J=3.4 Hz, 1H), 7.34 (d, J=3.4 Hz, 1H), 7.76 (d, J=1.7 Hz, 1H), 8.19 (d, J=1.7 Hz, 1H), 10.92 (br s, NH).

Workup

  1. concentrationAfter 20 min the mixture was concentrated
  2. custompartitioned between AcOEt and saturated aqueous NaHCO3 solution
  3. extractionThe aqueous layer was extracted with AcOEt (2×)
  4. dry with materialthe combined organic solutions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by PTLC

Sources & evidence

ORD record
ord-92b44a1636b84ea895ab22cde8dd4a35
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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