Triphenylphosphine → HCID 68585607, compound

HRID 2240739Notes

Reaction equation

HRID 2240739 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[N:12]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH:13]=1.[C:37]([N:44]1[CH2:49][CH2:48][CH:47](O)[CH2:46][CH2:45]1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:40]([O:39][C:37]([N:44]1[CH2:49][CH2:48][CH:47]([O:36][C:33]2[CH:34]=[CH:35][C:30]([C:27]3[CH:28]=[CH:29][C:24]([CH2:23][C:11]4[N:12]([C:14]5[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=5)[CH:13]=[C:9]([C:3]5[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=5[Cl:1])[N:10]=4)=[CH:25][CH:26]=3)=[CH:31][CH:32]=2)[CH2:46][CH2:45]1)=[O:38])([CH3:43])([CH3:41])[CH3:42]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 68583888HCID 68583888, compound

Product 1

HCID 68585607HCID 68585607, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Bromo-benzyl)-4-(2,4-dichlorophenyl)-1H-imidazole (3.27 g, 8.6 mmol) was treated as described in general procedure B using 4-fluoronitrobenzene to provide 2-(4-bromo-benzyl)-4-(2,4-dichloro-phenyl)-1-(4-nitro-phenyl)-1H-imidazole, which was treated with 4-hydroxyphenyl boronic acid according to general procedure G to provide 4′-[4-(2,4-dichloro-phenyl)-1-(4-nitro-phenyl)-1H-imidazol-2-ylmethyl]-biphenyl-4-ol (996 mg, 22% for two steps). To a solution of the phenol in THF (0.5 M) was added N-boc-4-hydroxypiperidine (2 eq) and triphenylphosphine (2 eq) under nitrogen, then while sonicating this mixture diisopropyl azodicarboxylate (2 eq) was added. After sonicating 1 hour the reaction mixture was evaporated in vacuo and the reside was purified by silica gel column chromatography to afford 4-{4′-[4-(2,4-dichloro-phenyl)-1-(4-nitro-phenyl)-1H -imidazol-2-ylmethyl]-biphenyl-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. additionwas added
  2. customAfter sonicating 1 hour the reaction mixture
  3. customwas evaporated in vacuo
  4. customthe reside was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9af9d20ef5584ca3835f0c4784d9ae99
Source dataset
uspto-grants-2010_05
Patent number
US07723369B2

Reaction notes

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