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

HRID 1994202Notes

Reaction equation

HRID 1994202 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)(C)C)(C)C)[C:5]2=[N:6][CH:7]=1.Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 497590181H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-

Product 1

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of the TBS derivative 26 (1.01 g, 3.3 mmol) in MeOH (10 mL) was added a 10% solution of HCl in MeOH (7 mL). After 8 min the solvents were evaporated and the residue was partitioned between AcOEt and saturated aqueous NaHCO3. The aqueous layer was extracted with AcOEt (3×). The combined organic solutions were dried (MgSO4), concentrated and purified by PTLC with CH2Cl2:MeOH=95:5 as eluent to afford the bromo derivative 27 (0.60 g, 94%). 1H NMR (400 MHz; CDCl3) δ 6.47 (dd, J=2.0, 3.5 Hz, 1H), 7.37 (dd, J=2.5, 3.5 Hz, 1H), 8.08 (d, J=2.0 Hz, 1H), 8.36 (d, J=2.0 Hz, 1H), 10.24 (br s, H).

Workup

  1. customAfter 8 min the solvents were evaporated
  2. customthe residue was partitioned between AcOEt and saturated aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with AcOEt (3×)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by PTLC with CH2Cl2

Sources & evidence

ORD record
ord-d78392cc14514f798e4620be09445c32
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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