Sodium Iodide → HCID 86723941, compound

HRID 1475309Notes

Reaction equation

HRID 1475309 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([O:17]C)[CH:16]=[C:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[I-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O.C(#N)C>[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15](=[O:17])[CH:16]=[C:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 24477Sodium ThiosulfateHCID 67133755HCID 67133755, compound

Product 1

HCID 86723941HCID 86723941, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-methoxy-2,3-dihydro-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (0.065 g, 0.26 mmol), benzyl bromide (0.053 g, 0.31 mmol), sodium iodide (0.077 g, 0.52 mmol) and acetonitrile (2 mL) was stirred at 60° C. for 40 h. The mixture was poured into a mixture of water (10 mL) and saturated aqueous sodium thiosulfate (10 mL) and extracted with DCM (3×20 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a brown oil. Chromatography (SiO2; gradient elution with 0-100% EtOAc in petrol) gave the title compound (0.054 g, ˜64%) as a colourless oil. MS: [M+H]+=327.

Workup

  1. extractionextracted with DCM (3×20 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give a brown oil
  5. washChromatography (SiO2; gradient elution with 0-100% EtOAc in petrol)

Sources & evidence

ORD record
ord-016a4c83e52b4d4892c3efa13d8a4395
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

Loading…