Water → HCID 59754776, compound

HRID 751434Notes

Reaction equation

HRID 751434 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/[CH:18]=C/C(O)=O)=[CH:4][CH:3]=1.[OH2:25]>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:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 59754787HCID 59754787, 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 LiA1H4 (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-b04e9fd37b8245ab9d9a02e7266ad12c
Source dataset
uspto-grants-2008_07
Patent number
US07405302B2

Reaction notes

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