Ethylene Glycol → HCID 178517865, compound

HRID 215960Notes

Reaction equation

HRID 215960 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22](I)[CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)CCC.[Cu]I.O>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[C:24]([N:15]2[CH2:16][CH2:17][C:10]3([C:9](=[O:18])[N:8]([C@H:5]4[CH2:4][CH2:3][C@@H:2]([OH:1])[CH2:7][CH2:6]4)[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)[CH:25]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 178517868HCID 178517868, compound

Product 1

HCID 178517865HCID 178517865, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(cis-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one (0.50 g, 2.0 mmol), 4-bromo-1-fluoro-2-iodobenzene (0.894 g, 2.97 mmol), copper(I) iodide (0.0586 g, 0.308 mmol), potassium phosphate (1.26 g, 0.596 mmol) and 1,2-ethanediol (0.23 mL, 4.1 mmol) in 1-butanol (2.5 mL) was heated at 100° C. overnight. The reaction mixture was treated with water, extracted with ether. The combined organic layers were washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure. The residue was purified on a silica gel column with ethyl acetate in hexane (gradient: 0 to 50%) to give the desired product (0.59 g, 70%). LCMS: (M+H)+=425.0/427.0.

Workup

  1. extractionextracted with ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified on a silica gel column with ethyl acetate in hexane (gradient: 0 to 50%)

Sources & evidence

ORD record
ord-d50c91e1934e43d382c73f612ede010c
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

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