Hydrochloric Acid → HCID 57537513, compound

HRID 1693734Notes

Reaction equation

HRID 1693734 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([C:14](=[O:20])[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])[CH:11]=[N:12][CH:13]=2)=[CH:6][N:5]=[C:4]2[N:21]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[CH:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[C:3]=12.Cl>CO.O.[OH-].[Pd+2].[OH-]>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:14]([OH:20])[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])[CH:11]=[N:12][CH:13]=2)=[CH:6][N:5]=[C:4]2[N:21]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:37])[CH3:38])[CH:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[C:3]=12

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57537682HCID 57537682, compound

Product 1

HCID 57537513HCID 57537513, compoundYield 108%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-N,N-dimethyl-2-oxo-acetamide (57 mg, 0.129 mmol) was dissolved in methanol (7 mL), and hydrochloric acid solution was added (774 μL, 0.774 mmol, 1.0 M solution in water). The flask was purged with nitrogen gas before and after addition of Palladium hydroxide (1.8 mg, 0.013 mmol, 20 weight % on carbon, wet) The flask was purged with hydrogen gas and allowed to stir for 15 hours at 23° C. under 1 atm of hydrogen gas. The reaction mixture was filtered through Celite® and concentrated to afford 2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-2-hydroxy-N,N-dimethyl-acetamide (79 mg, quantitative yield) as an orange-brown oil. MS [MH+] m/z: 573.0

Workup

  1. customThe flask was purged with nitrogen gas before and
  2. customwas purged with hydrogen gas
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74b6bc4a48ed4b439b5f4ad032ded33d
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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