3-Chlorophenol → HCID 10624176, compound

HRID 1585083Notes

Reaction equation

HRID 1585083 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH2:23][OH:24])=[C:9]2[CH3:25])=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:28]=[C:29](O)[CH:30]=[CH:31][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:26][C:27]1[CH:32]=[C:31]([CH:30]=[CH:29][CH:28]=1)[O:24][CH2:23][C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]=1[CH3:25]

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 105463821-(4-Fluorophenyl)-4-hydroxymethyl-5-methyl-2-(4-methylsulfonylphenyl)pyrrole

Product 1

HCID 10624176HCID 10624176, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-methanol (Example 21) (300 mg, 0.83 mmol), 3-chlorophenol (88 μl, 0.83 mmol), and triphenylphosphine (219 mg, 0.83 mmol) in THF (20 ml), diethyl azodicarboxylate (132 l, 0.83 mmol) was added. The mixture was stirred at room temperature for 48 hours. The solvent was removed under reduced pressure and the crude liquid (820 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 3-[(3-chlorophenoxy)methyl]-1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (75 mg, 19%): mp (DSC) 139° C. Anal Calc'd. for C25H21NSClFO3 : C, 63.89; H, 4.50; N, 2.98. Found: C, 63.85; H, 4.98; N, 2.76.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude liquid (820 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

Sources & evidence

ORD record
ord-4186e627ec5c4696be533e1af4cb5052
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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