Water → HCID 59299333, compound

HRID 2235290Notes

Reaction equation

HRID 2235290 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:8]2=[O:18])=[C:4]([Cl:21])[CH:3]=1.[Si]([C:26]#[N:27])(C)(C)C.O>CCN(CC)CC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:21][C:4]1[CH:3]=[C:2]([CH:20]=[CH:19][C:5]=1[CH2:6][CH:7]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:8]1=[O:18])[C:26]#[N:27]

Participants

6

Reactant 3

HCID 962WaterHCID 82115Trimethylsilyl cyanideHCID 116822063-(4-Bromo-2-chlorobenzyl)-1-cyclohexylpyrrolidin-2-one

Product 1

HCID 59299333HCID 59299333, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Dissolve 3-(4-bromo-2-chlorobenzyl)-1-cyclohexylpyrrolidin-2-one (Example 55) (0.50 g, 1.35 mmol) in Et3N (20 mL) under N2. Add Pd(PPh3)4 (0.32 g, 0.27 mmol), TMSCN (0.40 g, 4.05 mmol) with stirring. Heat the reaction mixture for 24 hours until LC-MS shows the starting material has gone. Cool the reaction to room temperature and add water (20 mL). Extract the aqueous with EtOAc (3×50 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 30-60% of EtOAc-Hexane) to give 0.42 g (98%) of the title compound as white solid: MS (APCI-pos mode) m/z (rel intensity) 317.2 (100), 319.2 (30).

Workup

  1. temperatureHeat the reaction mixture for 24 hours until LC-MS
  2. temperatureCool
  3. customthe reaction to room temperature
  4. extractionExtract the aqueous with EtOAc (3×50 mL)
  5. dry with materialCombine the organic layers and dry with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify by flash column chromatography (silica gel, 30-60% of EtOAc-Hexane)

Sources & evidence

ORD record
ord-3e88b62bba304734a85077c47acd82e2
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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