Triphenylphosphine → HCID 66739981, compound

HRID 1627306Notes

Reaction equation

HRID 1627306 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([SH:23])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:24][CH3:25].[F:26][C:27]1[CH:28]=[C:29]([CH:34]=[C:35]([F:39])[C:36]=1[CH2:37]O)[O:30][CH2:31][C:32]#[N:33].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:37][C:36]3[C:35]([F:39])=[CH:34][C:29]([O:30][CH2:31][C:32]#[N:33])=[CH:28][C:27]=3[F:26])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:24][CH3:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66741061HCID 66741061, compoundHCID 1784900045-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol

Product 1

HCID 66739981HCID 66739981, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (227 mg, 0.60 mmol), 2-(3,5-difluoro-4-(hydroxymethyl)phenoxy)acetonitrile (156 mg, 0.78 mmol), PPh3 (173 mg, 0.66 mmol) and DIAD (137 μL, 0.66 mmol) in THF (0.8 mL) were reacted, processed and purified by flash chromatography (80% EtOAc/Hex) to provide 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)acetonitrile (129 mg, 39%). MS (EI) m/z 558.3 (MH+).

Workup

  1. custompurified by flash chromatography (80% EtOAc/Hex)

Sources & evidence

ORD record
ord-8bebbcf28a83459487952e86de74de99
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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