Water → HCID 66728180, compound

HRID 573305Notes

Reaction equation

HRID 573305 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][O:22][CH3:23])=[CH:16][CH:15]=2)=[CH:6]1.C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C.O>C1(C)C=CC=CC=1>[CH3:23][O:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]2[C:8]3[N:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:5]3[C:6]=2[CH2:2][CH2:3][CH2:4]3)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547Azobisisobutyronitrile2×HCID 66728202HCID 66728202, compound

Product 1

HCID 66728180HCID 66728180, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 1-(3-bromopropyl)-3-[4-(methoxymethoxy)phenyl]-1H-pyrrolo[3,2-b]pyridine (486 mg), tri-n-butyltin hydride (0.697 mL), and AIBN (21.27 mg) in toluene (25 mL) was heated at 110° C. overnight. To the mixture was added AIBN (21.27 mg), and the mixture was heated at 110° C. for 2 h. The mixture was added to water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (88 mg).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-d1997cc6a4bf4f7ebc7cb915a67cef00
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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