Benzyl Alcohol → HCID 68682318, compound

HRID 2241556Notes

Reaction equation

HRID 2241556 reaction equation
[Cl-].C(C[P+](C)(C)C)#N.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:19](O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O:27]=[S:28]1(=[O:56])[CH2:33][CH2:32][N:31]([C:34]([C:36]2[NH:37][C:38]3[C:43]([CH:44]=2)=[CH:42][C:41]([C:45]([N:47]2[CH2:52][CH2:51][N:50]([CH:53]([CH3:55])[CH3:54])[CH2:49][CH2:48]2)=[O:46])=[CH:40][CH:39]=3)=[O:35])[CH2:30][CH2:29]1>C1(C)C=CC=CC=1>[CH2:19]([N:37]1[C:38]2[C:43](=[CH:42][C:41]([C:45]([N:47]3[CH2:48][CH2:49][N:50]([CH:53]([CH3:54])[CH3:55])[CH2:51][CH2:52]3)=[O:46])=[CH:40][CH:39]=2)[CH:44]=[C:36]1[C:34]([N:31]1[CH2:32][CH2:33][S:28](=[O:27])(=[O:56])[CH2:29][CH2:30]1)=[O:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 3251421Potassium bis(trimethylsilyl)amideHCID 57431663(Cyanomethyl)trimethylphosphonium chlorideHCID 68681206[2-(1,1-Dioxo-thiomorpholine-4-carbonyl)-1H-indol-5-yl]-(4-isopropyl-piperazin-1-yl)-methanone

Product 1

HCID 68682318HCID 68682318, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the suspension of 105 mg (0.70 mmol) (cyanomethyl)trimethylphosphonium chloride (prepared according to Tetrahedron Lett. 1996, 37 (14), 2459-62) in 1 mL toluene, 1.39 mL (0.70 mmol; 0.5M solution in toluene) potassium bis(trimethylsilyl)amide was added. After 10 min., 71 μL (74 mg, 0.70 mmol) benzylalcohol and 0.15 g (0.35 mmol) [2-(1,1-dioxo-thiomorpholine-4-carbonyl)-1H-indol-5-yl]-(4-isopropyl-piperazin-1-yl)-methanone (example 1) were added and the suspension was stirred for 1 h at reflux temperature. After cooling to room temperature the reaction mixture was evaporated to dryness, the residue was taken up in dichloromethane, filtered and the filtrate was evaporated. The crude product was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (19:1:0.1 v/v) as eluant to give 118 mg (65%) of the desired compound as a colorless foam.

Workup

  1. additionwas added
  2. temperatureat reflux temperature
  3. customwas evaporated to dryness
  4. filtrationfiltered
  5. customthe filtrate was evaporated
  6. customThe crude product was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (19:1:0.1 v/v) as eluant

Sources & evidence

ORD record
ord-4767de68d1e04581a58afdb8793ec70e
Source dataset
uspto-grants-2010_05
Patent number
US07723325B2

Reaction notes

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