4-(4-benzyloxy-phenoxy)-1H-pyrrolo[2,3-b]pyridine → 4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)phenol

HRID 491688Notes

Reaction equation

HRID 491688 reaction equation
C([O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][CH:21]=[CH:22][C:15]=23)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[NH:20]1[C:16]2=[N:17][CH:18]=[CH:19][C:14]([O:13][C:12]3[CH:23]=[CH:24][C:9]([OH:8])=[CH:10][CH:11]=3)=[C:15]2[CH:22]=[CH:21]1

Participants

4

Reactant 1

HCID 177555034-(4-benzyloxy-phenoxy)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 576785554-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 887MethanolSolvent

Procedure

4-(4-Benzyloxy-phenoxy)-1H-pyrrolo[2,3-b]pyridine (Step a, 9.0 g, 28.4 mmol, 1.0 eq.) was suspended into MeOH (200 mL) and the atmosphere was replaced by argon. 10% Pd/C (3 g total), was added and the argon was replaced by a H2 atmosphere. The mixture was stirred for 16 h at 60 psi at RT (using Parr shaker). The reaction showed about 50% conversion to product (monitored by HPLC). More 10% Pd/C was added and reacted another 16 h at 60 psi. More 10% Pd/C was added and reacted another 16 h at 60 psi. TLC showed reaction done. The Pd/C was filtered, the MeOH removed and the obtained 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenol was used crude in the next step.

Workup

  1. customreacted another 16 h at 60 psi
  2. customreacted another 16 h at 60 psi
  3. customreaction
  4. filtrationThe Pd/C was filtered
  5. customthe MeOH removed

Sources & evidence

ORD record
ord-7dbbda91d5084d369218f4d3ed9d30a3
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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