Nitrogen → HCID 57114858, compound

HRID 718660Notes

Reaction equation

HRID 718660 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.Cl.[NH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].N#N.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]([NH:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 12208p-DiiodobenzeneHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 57114858HCID 57114858, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1,4-diiodobenzene (33 g, 100 mmol) and tert-butyl 2-aminoacetate hydrochloride (25 g, 150 mmol) in DMF (100 mL) was purged with N2. Cut (19 g, 100 mmol) was added, followed by K2CO3 (35 g, 250 mmol). The reaction mixture was stirred overnight at 90° C. and allowed to cool to rt. The mixture was filtered through a pad of diatomaceous earth, and the filtrate was concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:25 v/v)) to obtain compound 56a as a red oil. Mass Spectrum (LCMS, ESI pos.): Calcd. for C12H16INO2: 334.2 (M+H). Found 334.0.

Workup

  1. additionwas added
  2. temperatureto cool to rt
  3. filtrationThe mixture was filtered through a pad of diatomaceous earth
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:25 v/v))

Sources & evidence

ORD record
ord-a4fae1ed5e0146d78647d418b4763f0f
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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