Methanol → 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylamino)nicotinic acid

HRID 888160Notes

Reaction equation

HRID 888160 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH:20]=O)=[CH:12]1.[BH4-].[Na+].CO>C1(C)C=CC=CC=1.O>[NH:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH2:20][NH:1][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:12]1

Participants

7

Reactant 4

HCID 887MethanolHCID 729302-Aminonicotinic acidHCID 4311764Sodium borohydrideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 692655932-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylamino)nicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-Aminonicotinic acid (945 mg, 6.85 mmol) was added to a suspension of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1 g, 6.85 mmol) in toluene (10 mL) under N2 atmosphere. A catalytic amount of tosyl acid was added to above and the mixture was heated to reflux for 3 h. The reaction was cooled to RT and NaBH4 was added. After stirring for 10 min., MeOH (2 ml) was added to above and the reaction was stirred for another 5 h at RT. The mixture was diluted with water and extracted with EtOAc. The aq layer was acidified using 1N HCl. The resultant precipitate was filtered and washed with AcCN affording compound as yellow solid.

Workup

  1. additionA catalytic amount of tosyl acid was added to above and the mixture
  2. temperaturewas heated
  3. temperatureto reflux for 3 h
  4. stirringwas stirred for another 5 h at RT
  5. extractionextracted with EtOAc
  6. filtrationThe resultant precipitate was filtered
  7. washwashed with AcCN affording compound as yellow solid

Sources & evidence

ORD record
ord-15373312f5d04da7956296e9c88cb035
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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