4-Fluorophenol → HCID 22054474, compound

HRID 1374748Notes

Reaction equation

HRID 1374748 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.Cl[C:16]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][OH:27])=[CH:23][CH:24]=2)[N:19]=[C:18]([CH3:28])[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:48][C:49]1[CH:54]=[CH:53][C:52](O)=[CH:51][CH:50]=1.[NH:56]1[CH2:60][CH2:59][CH2:58][CH2:57]1>ClCCl>[F:48][C:49]1[CH:54]=[CH:53][C:52]([O:27][CH2:26][C:22]2[CH:21]=[C:20]3[C:25]([C:16]([N:56]4[CH2:60][CH2:59][CH2:58][CH2:57]4)=[CH:17][C:18]([CH3:28])=[N:19]3)=[CH:24][CH:23]=2)=[CH:51][CH:50]=1

Participants

7

Reactant 5

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 31268PyrrolidineHCID 5363146Diisopropyl azodicarboxylateHCID 11264243HCID 11264243, compound

Product 1

HCID 22054474HCID 22054474, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylazodicarboxylate (97 mg, 0.48 mmol) was added dropwise at r.t. to a solution of (4-chloro-2-methyl-quinolin-7-yl)-methanol (example 2c, 100 mg, 0.48 mmol), triphenylphosphine (126 mg, 0.48 mmol), and 4-fluorophenol (54 mg, 0.54 mmol) in dichloromethane (2.5 mL). After shaking 24 h at r.t., the solvent was evaporated, and the residue was taken up in pyrrolidine (1.37 g, 19.2 mmol) and shaken for 23 h at 80° C. After cooling the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane, the organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 19:1) yielded the title compound (66 mg, 41%). Off-white solid, ISP-MS: m/e=337. ([M+H]+).

Workup

  1. customthe solvent was evaporated
  2. stirringshaken for 23 h at 80° C
  3. temperatureAfter cooling the reaction mixture
  4. customwas partitioned between sat. aq. ammonium chloride solution and dichloromethane
  5. washthe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-0aba429d26244c1287ca3d274ef5ac31
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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