Hydrochloric Acid → 1H-Pyrrolo(2,3-b)pyridine

HRID 1490237Notes

Reaction equation

HRID 1490237 reaction equation
C(O[C:6]([NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][N:10]=1)=O)(C)(C)C.C([Li])CCC.CN(C)C=O.Cl>O1CCCC1>[NH:8]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:14]2[CH:15]=[CH:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 117458482-(N-Boc-Amino)-3-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 92221H-Pyrrolo(2,3-b)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(tert-butoxycarbonylamino)-3-methylpyridine (Example 2a) (104.1 g, 0.5 mol) in tetrahydrofuran (2.0 liters) was cooled to -1° C. n-Butyllithium (2.5M, 400 ml, 1.0 mol) was added over 45 minutes (temp. ≤+5° C.) and the mixture aged at 0° C. to +3° C. for 1 hour. Dimethylformamide (39.2 ml, 0.51 mol) was added in one portion (temp. -3° C. to 9.9° C.), the mixture was stirred at +6° C. to +18° C. for 1 hour. The yellow suspension was transferred by canula, over 1 hour, into cooled (2.5° C.), vigorously stirred 5.5M hydrochloric acid (500 ml) at such a rate that the temperature was maintained at ≤10° C. The flask and transfer lines were washed through with 2M hydrochloric acid (200 ml) and the stirred mixture was heated at 45°-50° C. for 2 hours.

Workup

  1. additionwas added over 45 minutes (temp. ≤+5° C.)
  2. waitThe yellow suspension was transferred by canula, over 1 hour
  3. temperaturewas maintained at ≤10° C
  4. washThe flask and transfer lines were washed through with 2M hydrochloric acid (200 ml)
  5. temperaturethe stirred mixture was heated at 45°-50° C. for 2 hours

Sources & evidence

ORD record
ord-6c1cab8b96354950a0b180d25a7eed14
Source dataset
uspto-grants-1997_10
Patent number
US05681959

Reaction notes

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