3-(4-Benzyloxy-2-fluoro-5-methoxy-benzyl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine → 5-Fluoro-2-methoxy-4-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-phenol

HRID 1098479Notes

Reaction equation

HRID 1098479 reaction equation
C([O:8][C:9]1[C:34]([O:35][CH3:36])=[CH:33][C:12]([CH2:13][C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH:15]=2)=[C:11]([F:37])[CH:10]=1)C1C=CC=CC=1>CO.O1CCCC1.[Pd]>[F:37][C:11]1[C:12]([CH2:13][C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([Si:23]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:30]([CH3:32])[CH3:31])[CH:15]=2)=[CH:33][C:34]([O:35][CH3:36])=[C:9]([OH:8])[CH:10]=1

Participants

5

Reactant 1

HCID 580864183-(4-Benzyloxy-2-fluoro-5-methoxy-benzyl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 580865995-Fluoro-2-methoxy-4-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-phenolYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Benzyloxy-2-fluoro-5-methoxy-benzyl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (657, 0.831 g, 1.60 mmol) was dissolved in methanol (40 mL) and tetrahydrofuran (40 mL). 10% Palladium on carbon (3.41 g) was added. The reaction was shaken at 50 psi for 1 hour. The reaction was filtered through Celite and washed with methanol. The organic portion was passed through celite several times until a clear solution was obtained. The organic portion was concentrated under reduced pressure to provide the desired compound as an off-white solid (649, 587 mg, 86%). MS (ESI) [M+H+]+=429.5.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. washwashed with methanol
  3. customwas obtained
  4. concentrationThe organic portion was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d831afca01144c3e8eabf35cbce07cbf
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

Loading…