Potassium Carbonate → HCID 70664411, compound

HRID 1026651Notes

Reaction equation

HRID 1026651 reaction equation
[CH2:1]([N:8]1[CH2:16][C@H:15]2[C@:10]([CH3:23])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[C:19](Br)[CH:18]=[CH:17][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl>[CH2:1]([N:8]1[CH2:16][C@H:15]2[C@:10]([CH3:23])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[C:19]([CH3:24])[CH:18]=[CH:17][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 70665186HCID 70665186, compound

Product 1

HCID 70664411HCID 70664411, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of cis-2-benzyl-7-bromo-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.154 mmol, 60 mg), tetrakis(triphenylphosphine)Pd(0) (7.68 μmol, 8.96 mg), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.184 mmol, 52 μl, 46.3 mg) and potassium carbonate (0.230 mmol, 32.2 mg) in 1,4-Dioxane (1 ml) and Water (0.5 ml) was heated in a microwave reactor at 130° C. for 20 min. The reaction mixture was diluted with DCM and water, the phases were separated and the aqueous was extracted with DCM (using a hydrophobic frit). The combined organic extracts were concentrated in vacuo and purified by silica column chromatography (eluting with neat heptane—2:1 heptane:ethyl acetate). The fractions containing the product compound were concentrated in vacuo and then redissolved in MeOH and then passed through Strata SCX column (1 g) and concentrated in vacuo to afford cis-2-benzyl-6-chloro-3a,7-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (39.4 mg), m/z=326.2 [M+H]+.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous was extracted with DCM (
  3. concentrationThe combined organic extracts were concentrated in vacuo
  4. custompurified by silica column chromatography (eluting with neat heptane—2:1 heptane:ethyl acetate)
  5. additionThe fractions containing the product compound
  6. concentrationwere concentrated in vacuo
  7. dissolutionredissolved in MeOH
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11c548299d634584b9340cf9d4a11da3
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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