Trimethylphosphine → HCID 68763036, compound

HRID 1875236Notes

Reaction equation

HRID 1875236 reaction equation
[N:1]([C:4]1[N:5]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][C:22]3[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([Cl:30])[CH:23]=3)[C:15]=2[F:31])=[O:11])=[C:7]([Cl:9])[N:8]=1)=[N+]=[N-].[CH3:40][P:41]([CH3:43])[CH3:42]>C1COCC1>[Cl:9][C:7]1[N:8]=[C:4]([N:1]=[P:41]([CH3:43])([CH3:42])[CH3:40])[N:5]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:6]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][C:22]2[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([Cl:30])[CH:23]=2)[C:15]=1[F:31])=[O:11]

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 86761665HCID 86761665, compound

Product 1

HCID 68763036HCID 68763036, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of 2-azido-4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (1.86 g, 3.05 mmol) in THF (25 ml) was added a 1M solution of trimethylphosphine in THF (6.10 ml, 6.10 mmol). Gas evolution occurred and the reaction mixture was stirred at RT for 1 h. The reaction mixture was evaporated and taken up in EtOAc and water. The organic phase was dried (Na2SO4), filtered and evaporated to provide the title compound (1.96 g, 97%) as an off-white foam.

Workup

  1. customThe reaction mixture was evaporated
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-73239471bec64b58b1b4b56f33063f87
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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