Water → (4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol

HRID 1445921Notes

Reaction equation

HRID 1445921 reaction equation
C([O:3][C:4]([C:6]1[NH:16][C:9]2=[N:10][CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]2[CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[CH3:15][O:14][C:13]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:16][C:6]([CH2:4][OH:3])=[CH:7][C:8]=12

Participants

5

Reactant 3

HCID 962WaterHCID 11736140Ethyl 4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15885418(4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-ethoxycarbonyl-4-methoxypyrrolo-[2,3-b]pyridine 3 (1.90 g, 8.62 mmol) in anhydrous THF (25 mL) was added LiAlH4 (0.218 g, 17.2 mmol) in small portions under N2 atmosphere. The mixture was stirred at reflux temperature for 50 min. After cooling, it was poured into cool H2O (20 mL) and extracted with EtOAc (4×15 mL). The combined organic layers were washed with brine (20 mL) and dried (Na2SO4). After filtration, the filtrate was concentrated to dryness and the residue was chromatographed on a silica gel column using 5% methanol in CH2Cl2 to give 4 as white solid. Mp 210-212° C.; Yield: 1.10 g, 71%; ESI MS: m/z 178.9 (M+1).

Workup

  1. temperatureat reflux temperature for 50 min
  2. temperatureAfter cooling
  3. additionit was poured
  4. extractionextracted with EtOAc (4×15 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated to dryness
  9. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-8352612334784a799eb692168d287650
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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