(4-Cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol → HCID 54562985, compound

HRID 278183Notes

Reaction equation

HRID 278183 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[N:12]=[CH:13][N:14]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:15]=2)[OH:10])=[CH:5][C:4]=1[F:35])#[N:2]>C(Cl)Cl.O=[Mn]=O>[C:29]1([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:14]2[CH:15]=[C:11]([C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:35])[CH:5]=3)=[O:10])[N:12]=[CH:13]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 11134299(4-Cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol

Product 1

HCID 54562985HCID 54562985, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol from Step D (10.0 g, 21.8 mmol) in CH2Cl2 (300 mL) was added MnO2 (18.9 g, 218 mmol) and the resulting mixture was heated to reflux for 18 hrs. The mixture was allowed to cool, then filtered through a pad of celite, washing with CH2Cl2. The filtrate was concentrated under reduced pressure to provide the titled product as a white solid that was sufficiently pure for use in the next step.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 18 hrs
  3. temperatureto cool
  4. filtrationfiltered through a pad of celite
  5. washwashing with CH2Cl2
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-459d4844b59743eab0b9371f431ccad0
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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