Hydrochloric Acid → HCID 69458461, compound

HRID 1351989Notes

Reaction equation

HRID 1351989 reaction equation
[Si:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][C:19]#[N:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl>O1CCCC1.C(O)C.[Ni]>[Si:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][CH2:19][NH2:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 69456027HCID 69456027, compound

Product 1

HCID 69458461HCID 69458461, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 702EthanolSolventHCID 935NickelSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-1-yl)acetonitrile (259 mg, 0.904 mmol) in tetrahydrofuran (20 mL) are added a 2.0M hydrochloric acid in ethanol (1 mL) and active Raney-nickel (manufactured by Kawaken Fine Chemicals Co., Ltd., about 1 mL), and the mixture is vigorously stirred under hydrogen atmosphere under pressure (0.5 Pa) at room temperature for 1 hour. To the mixture is further added active Raney-nickel (about 1.5 mL), and the mixture is vigorously stirred under the same conditions for 4 hours. The catalyst is removed by filtration through celite, and the filtrate is concentrated under reduced pressure. The obtained residue is purified by silica gel column (ammonia-chloroform:methanol=100:1→50:1→30:1) to give the title compound as pale brown oil (207 mg, yield: 79%).

Workup

  1. stirringthe mixture is vigorously stirred under the same conditions for 4 hours
  2. customThe catalyst is removed by filtration through celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe obtained residue is purified by silica gel column (ammonia-chloroform:methanol=100:1→50:1→30:1)

Sources & evidence

ORD record
ord-1e3c06b5bfe3437599bb87ce5c9267d5
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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