Binol → HCID 86706877, compound

HRID 874727Notes

Reaction equation

HRID 874727 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.C(O)(=O)C(O)=O.[CH2:15]1[C:18]2([CH2:21][NH:20][CH2:19]2)[CH2:17][O:16]1.C1C=CC2C(C3C(O)=CC=C4C=3C=CC=C4)=C(O)C=CC=2C=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.CCOC(C)=O.[Cu]I>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:20]2[CH2:21][C:18]3([CH2:15][O:16][CH2:17]3)[CH2:19]2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 11762BinolHCID 12208p-DiiodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 53308464Oxalic acid--2-oxa-6-azaspiro(3.3)heptane (1/1)

Product 1

HCID 86706877HCID 86706877, compoundYield 37.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was synthesized according to General Method D, utilizing 1,4-diiodobenzene (2.5 g, 7.6 mmol), 2-oxa-6-azaspiro[3.3]heptane oxalic acid salt (1.0 g, 6.9 mmol), CuI (0.26 g, 1.4 mmol), BINOL (0.40 g, 1.4 mmol), and K3PO4 (4.4 g, 21 mmol) in DMF (15 mL). The mixture was diluted with EtOAc, filtered through Celite and the filtrate was concentrated. Purification by flash chromatography (Biotage Isolera, 100 g HP-SIL, 10-50% EtOAc in hexanes) gave the title compound as a yellow solid (0.78 g, 37%). 1H NMR (400 MHz, CDCl3) δ ppm 7.47 (d, J=8.8 Hz, 2H), 6.22 (d, J=8.8 Hz, 2H), 4.82 (s, 4H), 3.98 (s, 4H); MS ESI 301.9 [M+H]+, calcd for [C11H12INO+H]+ 302.0.

Workup

  1. customThe title compound was synthesized
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate was concentrated
  4. customPurification by flash chromatography (Biotage Isolera, 100 g HP-SIL, 10-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4d925c90d21f43999dc58304b6c6d288
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

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