1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69526653, compound

HRID 1829807Notes

Reaction equation

HRID 1829807 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1CCN2C(=NCCC2)CC1.[CH2:39]([O:46][C:47]1[CH:48]=[C:49]2[C:53](=[CH:54][CH:55]=1)[N:52]([CH3:56])[C:51]([CH:57]=O)=[CH:50]2)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(#N)C>[CH2:39]([O:46][C:47]1[CH:48]=[C:49]2[C:53](=[CH:54][CH:55]=1)[N:52]([CH3:56])[C:51]([CH:57]=[CH:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[CH:50]2)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734970Benzyltriphenylphosphonium bromideHCID 11043675HCID 11043675, compound

Product 1

HCID 69526653HCID 69526653, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under N2, to a suspension of benzyltriphenylphosphonium bromide (980 mg, 2.26 mmol) in acetonitrile (10 ml) was added DBU at room temperature. After stirring for 10 min., 5-(benzyloxy)-1-methyl-1H-indole-2-carbaldehyde (500 mg, 1.88 mmol) was added and the mixture was stirred overnight at room temperature. The resulting mixture was filtered and washed with acetonitrile. The filtrate was concentrated in vacuo and then the residue was purified by silica gel (70 g) chromatography eluted with chloroform to give 5-(benzyloxy)-1-methyl-2-(2-phenylethenyl)-1H-indole (221 mg, 34.5%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationThe resulting mixture was filtered
  3. washwashed with acetonitrile
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel (70 g) chromatography
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-4f14afdf14944e8ea1143f7696934d1a
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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