Sodium Carbonate → HCID 66728062, compound

HRID 573265Notes

Reaction equation

HRID 573265 reaction equation
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([CH3:11])[CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([O-:14])=[O:13].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][N:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2]([C:18]2[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)=[CH:3]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 667278953-bromo-1-methyl-1H-Pyrrolo[3,2-b]pyridine

Product 1

HCID 66728062HCID 66728062, compoundYield 37.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine (200 mg), (4-nitrophenyl)boronic acid (175 mg), Pd(PPh3)4 (95 mg) and Na2CO3 (201 mg) in DME (4 mL) and water (2 mL) was heated at 100° C. for 19 h. After this time, the reaction was cooled to room temperature, diluted with AcOEt (100 mL), washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (heptane to 1:1 AcOEt/heptane) to give the title compound (89 mg).

Workup

  1. temperatureAfter this time, the reaction was cooled to room temperature
  2. washwashed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography (heptane to 1:1 AcOEt/heptane)

Sources & evidence

ORD record
ord-9dc8ae946d9746adbd26d72514820ecf
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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