Benzyl Alcohol → HCID 68682318, compound

HRID 1820396Notes

Reaction equation

HRID 1820396 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-d6612a2a3e984638a85cde2b18bab0d2
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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