Ethyl Acetate → N-{4-[5-(3,4,5-Trimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-benzyl}-acetamide

HRID 85057Notes

Reaction equation

HRID 85057 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:21]=[CH:20][C:14]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[CH3:32][O:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[C:38]([O:42][CH3:43])[C:39]=1[O:40][CH3:41].C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>CC#N.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:43][O:42][C:38]1[CH:37]=[C:36]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[CH:21]=[CH:20][C:14]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=4)=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:35]=[C:34]([O:33][CH3:32])[C:39]=1[O:40][CH3:41]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 66779757HCID 66779757, compound

Product 1

HCID 54764743N-{4-[5-(3,4,5-Trimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-benzyl}-acetamideYield 53.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

N-{4-[5-Bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-benzyl}-acetamide (Intermediate CC, 24 mg, 0.048 mmol), 3,4,5-trimethoxyphenyl boronic acid (13 mg, 0.058 mmol) and dichlorobis(triphenylphosphine)palladium (II) (2 mg, 0.002 mmol) were combined in CH3CN (1 ml) and 1 M Na2CO3 (2 ml) and heated in a microwave reactor at 150° C. for 20 min. EtOAc was added, washed with water, dried and purified by silica gel chromatography eluting with 0-4% MeOH:DCM to give 11 mg (53%) of the title compound.

Workup

  1. washwashed with water
  2. customdried
  3. custompurified by silica gel chromatography
  4. washeluting with 0-4% MeOH

Sources & evidence

ORD record
ord-b9b174b33cef41e4ad2a2d407fefdec4
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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