Acetic Acid → HCID 59803874, compound

HRID 253479Notes

Reaction equation

HRID 253479 reaction equation
C([O:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]([CH2:13][C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[NH:16][CH:15]=2)=[C:11]([F:28])[CH:10]=1)C1C=CC=CC=1.C(O)(=O)C>O1CCCC1.[Pd]>[Cl:23][C:20]1[CH:21]=[C:22]2[C:14]([CH2:13][C:12]3[C:11]([F:28])=[CH:10][C:9]([OH:8])=[C:25]([O:26][CH3:27])[CH:24]=3)=[CH:15][NH:16][C:17]2=[N:18][CH:19]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59803827HCID 59803827, compound

Product 1

HCID 59803874HCID 59803874, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Benzyloxy-2-fluoro-5-methoxy-benzyl)-5-chloro-1H-pyrrolo[2,3-b]pyridine (224, 48 mmol) was dissolved in tetrahydrofuran (300 mL) and 20% palladium on carbon (50% water wet, 2.3 g) was added. The mixture was stirred under an atmosphere of hydrogen at 50 psi in the presence of acetic acid (100 mL). The reaction mixture was filtered through Celite and evaporated to dryness to give the desired compound 225. MS (ESI) [M+H+]+=307.1.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-4d5ed485a0594ecaab27d9f520aeb9a9
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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