Water → HCID 59754776, compound

HRID 1713416Notes

Reaction equation

HRID 1713416 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:10]3[CH:9]=[C:8]2[C:18](OCC)=[O:19])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:10]3[CH:9]=[C:8]2[CH2:18][OH:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59754791HCID 59754791, compound

Product 1

HCID 59754776HCID 59754776, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To Ethyl 1-(4-chloro-benzyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate from step 4 (170 mg, 0.493 mmol) in THF (4 mL), was added LiAlH4 (21 mg, 0.542 mmol) and heated to reflux for 30 min. After cooling, the reaction mixture was poured into water, extracted with EtOAc (4×25 mL), the organic phase dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on silica gel eluting with a gradient of 0 to 40% EtOAc in hexanes to yield the title alcohol.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc (4×25 mL)
  5. dry with materialthe organic phase dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified on silica gel eluting with a gradient of 0 to 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-f2212a9889c444fcaaa4f2af2110a638
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

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