Tributylphosphine → HCID 59242951, compound

HRID 423209Notes

Reaction equation

HRID 423209 reaction equation
[Br:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[I:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH2:8][O:9][C:16]2[CH:15]=[C:14]([Cl:17])[CH:13]=[CH:12][C:11]=2[I:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 66133335-chloro-2-iodophenolHCID 14022521(3-Bromopyridin-2-yl)methanol

Product 1

HCID 59242951HCID 59242951, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(3-Bromo-pyridin-2-yl)-methanol (3.4 g, 18 mmol), and 2-iodo-5-chlorophenol 4.5 g, 18 mmol), are dissolved in benzene (60 mL) and cooled to 0° C. To the solution is added tributylphosphine (15 mL, 90 mmol), and 1,1′-(azodicarbonyl) dipiperidine (ADDP) (6.6 g, 18 mmol) and the mixture is heated at 40° C. for 3 h. The reaction mixture is diluted with ethyl acetate, washed with saturated aqueous NH4Cl and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage® Si65M, 15% ethyl acetate/hexane) to yield 3.77 g (51%) of the title compound as a white solid. GCMS m/e 296, 298 [M-I]−.

Workup

  1. temperaturethe mixture is heated at 40° C. for 3 h
  2. washwashed with saturated aqueous NH4Cl and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash chromatography (Biotage® Si65M, 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3abff213d76c4d6198aae4913573ee7d
Source dataset
uspto-grants-2012_01
Patent number
US08101760B2

Reaction notes

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