Water → HCID 58914703, compound

HRID 1297798Notes

Reaction equation

HRID 1297798 reaction equation
[C:1]([Si:5]([CH3:42])([CH3:41])[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])=[C:26]([CH3:39])[CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])=[CH:9][C:8]=1[CH3:40])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:50][C:51]#[N:52].O>CN(C=O)C.C1COCC1.C(OCC)C>[C:1]([Si:5]([CH3:42])([CH3:41])[O:6][C:7]1[C:8]([CH3:40])=[CH:9][C:10]([C:14]2([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([O:31][Si:32]([C:35]([CH3:36])([CH3:38])[CH3:37])([CH3:33])[CH3:34])=[C:26]([CH3:39])[CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:50][C:51]#[N:52])[C:15]2=[O:23])=[CH:11][C:12]=1[CH3:13])([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 11534BromoacetonitrileHCID 23665647Potassium tert-butoxideHCID 58914719HCID 58914719, compound

Product 1

HCID 58914703HCID 58914703, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under an N2 atmosphere, dissolve 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (2.5 g, 4.15 mmol) in dry DMF (50 mL). Cool the reaction to 0° C. Add a solution of potassium t-butoxide (1.0 M) in THF (4.57 mL). Allow the reaction to stir at 0° C. for 10 minutes. Add bromoacetonitrile (0.32 mL, 4.57 mmol), and allow the reaction to warm to room temperature. Stir the reaction at room temperature overnight. Dilute the reaction with water (200 mL) and diethyl ether (200 mL). Separate the layers and wash the aqueous layer with diethyl ether (100 mL). Combine the organic layers. Wash the diethyl ether with brine (100 mL), and separate the layers. Dry the organic layer with sodium sulfate and concentrate in vacuo. Purify the crude oil by flash column chromatography. Elute the column with 20% ethyl acetate in hexanes to give 1.92 g (72%) of the title compound: 1H NMR(CDCl3): δ7.36 (td, 1H), 7.29-7.26 (m, 1H), 7.17 (td, 1H), 7.06 (d, 1H), 6.77 (s, 4H), 4.72 (s, 2H), 2.12 (s, 12H), 1.01 (s, 18H), 0.16 (s, 6H) 0.16 (s, 6H).

Workup

  1. temperatureCool
  2. customthe reaction to 0° C
  3. customthe reaction
  4. customthe reaction
  5. temperatureto warm to room temperature
  6. stirringStir
  7. customthe reaction at room temperature overnight
  8. additionDilute
  9. customSeparate the layers
  10. washwash the aqueous layer with diethyl ether (100 mL)
  11. washWash the diethyl ether with brine (100 mL)
  12. customseparate the layers
  13. dry with materialDry the organic layer with sodium sulfate
  14. concentrationconcentrate in vacuo
  15. customPurify the crude oil by flash column chromatography
  16. washElute the column with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d861a04b8244439fabb5826e76388bb9
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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