4-Iodophenol → 1-(4-Fluorophenyl)-3-(4-iodophenoxy)methyl-2-methyl-5-(4-methylsulfonylphenyl)pyrrole

HRID 1937358Notes

Reaction equation

HRID 1937358 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.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:57][C:58]1[CH:63]=[CH:62][C:61](O)=[CH:60][CH:59]=1>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH2:23][O:24][C:61]3[CH:62]=[CH:63][C:58]([I:57])=[CH:59][CH:60]=3)=[C:9]2[CH3:25])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 108944-IodophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 105463821-(4-Fluorophenyl)-4-hydroxymethyl-5-methyl-2-(4-methylsulfonylphenyl)pyrrole

Product 1

HCID 224606791-(4-Fluorophenyl)-3-(4-iodophenoxy)methyl-2-methyl-5-(4-methylsulfonylphenyl)pyrrole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 6 (from Example A) (1 mmol) is added to a solution of diethylazodicarboxylate (1 mmol), triphenylphosphine (1 mmol) and 4-iodophenol (1 mmol) in dry THF (25 mL). The progress of the reaction is monitored by tlc. When the reaction is complete, water is added and the crude product is extracted in ethyl acetate. The extract is dried and evaporated and the title compound 25 is purified by HPLC.

Workup

  1. extractionthe crude product is extracted in ethyl acetate
  2. customThe extract is dried
  3. customevaporated
  4. customthe title compound 25 is purified by HPLC

Sources & evidence

ORD record
ord-6d9cd3565f084a96b6b308e00ec90878
Source dataset
uspto-grants-2002_05
Patent number
US06395724B1

Reaction notes

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