Diiodomethane → HCID 67172047, compound

HRID 450110Notes

Reaction equation

HRID 450110 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)=[CH:2]1.[CH2:22]([Zn]CC)C.ICI>C(Cl)Cl.CCCCCC>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]23[CH2:22][CH:14]2[CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)=[CH:2]1

Participants

6

Reactant 3

HCID 6346DiiodomethaneHCID 67172412HCID 67172412, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 67172047HCID 67172047, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of tert-butyl 3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (700 mg, 2.5 mmol) in DCM (20 mL), was added dropwise at 0° C. under nitrogen atmosphere diethylzinc (6.13 mL of a 1M solution in hexane, 6.1 mmol) and diiodomethane (0.79 mL, 9.8 mmol). The mixture was warmed to RT and stirred at RT overnight. The mixture was then cooled with an ice bath and quenched with a saturated aqueous solution of ammonium chloride. The mixture was extracted with DCM, dried over sodium sulphate and concentrated in vacuo. The residue was triturated in diisopropylether and the resulting precipitate was filtered and then purified by column chromatography (DCM/MeOH 95:5) to afford the title compound as a yellow solid (100 mg).

Workup

  1. temperatureThe mixture was then cooled with an ice bath
  2. customquenched with a saturated aqueous solution of ammonium chloride
  3. extractionThe mixture was extracted with DCM
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in diisopropylether
  7. filtrationthe resulting precipitate was filtered
  8. custompurified by column chromatography (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-cdca724b877c49808d90dc0610d91e65
Source dataset
uspto-grants-2013_07
Patent number
US08486964B2

Reaction notes

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