Toluene → HCID 89618125, compound

HRID 1502570Notes

Reaction equation

HRID 1502570 reaction equation
Br[C:2]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:3]=1[CH2:4][CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]12.[C:22]1(C)[CH:27]=CC=C[CH:23]=1>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>[CH2:27]([C:2]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:3]=1[CH2:4][CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]12)[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 1140TolueneHCID 67989352HCID 67989352, compound

Product 1

HCID 89618125HCID 89618125, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution tert-butyl 5-bromo-2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate (Step 3, 500 mg), Pd(PPh3)4 (80 mg, 0.1 equiv.), allyltributylstannate (0.56 g, 1.20 equiv.) in toluene (17 mL) was degassed and stirred at reflux overnight. The solvent was removed under vacuum. The residue was taken up in acetonitrile (40 mL) and washed twice with n-hexane. The acetonitrile was removed in vacuo and the residue was purified by flash chromatography eluting with ethyl acetate and cyclohexane (1 to 25%) to give 210 mg of the desired product E1; LCMS (Method B), RT: 1.05 min; ES+ 649 (2M+Na+).

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed under vacuum
  3. washwashed twice with n-hexane
  4. customThe acetonitrile was removed in vacuo
  5. customthe residue was purified by flash chromatography
  6. washeluting with ethyl acetate and cyclohexane (1 to 25%)

Sources & evidence

ORD record
ord-b3f96b33a4b542deaf1d4d4a29ef6753
Source dataset
uspto-grants-2015_12
Patent number
US09210929B2

Reaction notes

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