4-Iodo-1-tritylimidazole → (4-Cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol

HRID 2306214Notes

Reaction equation

HRID 2306214 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C[Mg+].[Br-].[C:29]([C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][C:32]=1[F:39])#[N:30]>C(Cl)Cl.CCOCC.C1COCC1>[C:29]([C:31]1[CH:38]=[CH:37][C:34]([CH:35]([C:2]2[N:3]=[CH:4][N:5]([C:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:6]=2)[OH:36])=[CH:33][C:32]=1[F:39])#[N:30]

Participants

7

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 112173392-Fluoro-4-formylbenzonitrileHCID 178418689HCID 178418689, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-iodo-1-(triphenylmethyl)imidazole (2.93 g, 6.71 mmol) in dry CH2Cl2 (30 mL), under argon, was added MeMgBr (2.35 mL of a 3.0M solution in Et2O, 7.05 mmol), dropwise. The resulting solution was stirred at ambient temperature for 1 hour, then transferred dropwise into a stirred solution of 4-cyano-3-fluorobenzaldehyde, as described in Example 11, Step B, (1.00 g, 6.71 mmol) in dry THF (30 mL), under argon, at −78° C. After 30 min, the reaction mixture was quenched with saturated aqueous NH4Cl (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with EtOAc to yield the desired alcohol as a white solid.

Workup

  1. waitAfter 30 min
  2. customthe reaction mixture was quenched with saturated aqueous NH4Cl (50 mL)
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with EtOAc

Sources & evidence

ORD record
ord-b0ac32b34e294f5b8e6aa7ab0f6b77e8
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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