Methoxymethyl-triphenylphosphonium chloride → HCID 59146072, compound

HRID 1512793Notes

Reaction equation

HRID 1512793 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:24][Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:34][C:35]1[CH:36]=[C:37]([C:45]2[O:49][N:48]=[C:47]([C:50]3[CH:51]=[CH:52][CH:53]=[C:54]4[C:58]=3[N:57]([CH3:59])[CH:56]=[C:55]4C=O)[N:46]=2)[CH:38]=[CH:39][C:40]=1[O:41][CH:42]([CH3:44])[CH3:43]>CS(C)=O>[Cl:34][C:35]1[CH:36]=[C:37]([C:45]2[O:49][N:48]=[C:47]([C:50]3[CH:51]=[CH:52][CH:53]=[C:54]4[C:58]=3[N:57]([CH3:59])[CH:56]=[C:55]4/[CH:24]=[CH:4]/[O:3][CH3:2])[N:46]=2)[CH:38]=[CH:39][C:40]=1[O:41][CH:42]([CH3:43])[CH3:44]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 591461277-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 59146072HCID 59146072, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (methoxymethyl)triphenylphosphonium chloride (2.9 g) in dimethyl sulfoxide (20 mL) stirred under nitrogen at 20° C. was added a solution of NaHMDS (8.6 mL, 1.0 mol/L in THF) dropwise during 5 mins. The reaction mixture was stirred at this temperature for 20 mins. Then 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D87) (1.4 g) was added in one portion. The mixture was stirred at room temperature for 30 mins. The reaction mixture was quenched with water, partitioned between ether (100 mL) and water (50 mL). The organic phase was washed with water and brine, dried over sodium sulphate and evaporated to afford 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-3-[(E)-2-(methyloxy)ethenyl]-1H-indole (D87) as a brown oil (3.8 g), used directly in the next step. MS (ES): C23H22ClN3O3 requires 423; found 424.2 (M+H+).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 mins
  2. customThe reaction mixture was quenched with water
  3. custompartitioned between ether (100 mL) and water (50 mL)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-6caad47c46d046e68b63f0f062d6e886
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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