Toluene → HCID 67989354, compound

HRID 1844088Notes

Reaction equation

HRID 1844088 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:21]=1[CH:9]1[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11](=[O:13])[CH2:12][CH:8]1[CH2:7]2.[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:3]=[CH:4][CH:5]=[C:6]2[C:21]=1[CH:9]1[N:10]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C:11](=[O:13])[CH2:12][CH:8]1[CH2:7]2)[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 1140TolueneHCID 67975402HCID 67975402, compound

Product 1

HCID 67989354HCID 67989354, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution tert-butyl 8-bromo-2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate (Example F10, 700 mg), Pd(PPh3)4 (280 mg, 0.12 equiv.), allyltributylstannate (1.65 g, 2.5 equiv.) in toluene (17 mL) was degassed and stirred at reflux over night. 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 350 mg of the desired products (mixture of allyl and isomer) F14: LCMS (method E), RT: 1.06 min, [ES+[377, M+CH3CN+Na].

Workup

  1. temperatureat reflux over night
  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-4250f26ee3304fd29c82271ab3b2c3ac
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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