2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-Acetyl-1-ethyl-6-methoxy-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine

HRID 1421266Notes

Reaction equation

HRID 1421266 reaction equation
[CH2:1]([C:3]1[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][N:6]2[C:11]=1[CH:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2)[CH3:2].[CH3:22][C:23](=[O:26])[C:24]#[CH:25].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[C:23]([C:24]1[CH:25]=[C:5]2[N:6]3[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=13)[C:3]([CH2:1][CH3:2])=[C:4]2[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:26])[CH3:22]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15018Butyn-2-oneHCID 11108777HCID 11108777, compound2×

Product 1

HCID 187806374-Acetyl-1-ethyl-6-methoxy-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizineYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-ethyl-7-methoxy-2-(4-methoxyphenyl)indolizine (Compound 3) (2.0 g, 7.11 mmol) in 65 ml of toluene was stirred in an ice bath, while 3-butyn-2-one (0.64 ml, 8.17 mmol) was added dropwise. The cooling source was removed and stirring was continued for twenty hours. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (1.73 g, 7.61 mmol) was added in portions and stirring was continued for twenty hours. The solvent was evaporated and the residue chromatographed over aluminium oxide with heptane/tetrahydrofuran (1:1) as eluent to afford 1.54 g (63%) of the title compound. M.p. 137-39° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.39 (t, 3H), 2.64 (s, 3H), 3.15 (q, 2H), 3.87 (s, 3H), 4.09 (s, 3H), 7.19 (d, 2H), 7.80 (d, 2H), 7.82 (d, 1H), 7.89 (d, 1H), 8.15 (s, 1H). (Compound 6).

Workup

  1. additionwas added dropwise
  2. customThe cooling source was removed
  3. waitwas continued for twenty hours
  4. stirringstirring
  5. waitwas continued for twenty hours
  6. customThe solvent was evaporated
  7. customthe residue chromatographed over aluminium oxide with heptane/tetrahydrofuran (1:1) as eluent

Sources & evidence

ORD record
ord-9e10466c34f74dcfa12b5924e442beb4
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

Loading…