Pentane → HCID 68284413, compound

HRID 1527189Notes

Reaction equation

HRID 1527189 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.CCCCC.[Cl-].[C:17]([O:21][C:22](=[O:25])[CH2:23][Zn+])([CH3:20])([CH3:19])[CH3:18]>C1COCC1.CCOC(C)=O>[C:17]([O:21][C:22](=[O:25])[CH2:23][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 8003PentaneHCID 6764936-BromoindoleHCID 178451183HCID 178451183, compound

Product 1

HCID 68284413HCID 68284413, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromoindole (2 g, 10.2 mmol) in THF (20 mL) under nitrogen atmosphere was added KH (30% in mineral oil de-greased with pentane, 1.5 g, 11.22 mmol) and the mixture was stirred at RT for 30 min before addition of [P(t-Bu)3PdBr]2 (40 mg, 0.051 mmol) diluted in THF (20 mL). The resulting mixture was added to a solution of 2-tert-butoxy-2-oxoethylzinc chloride (0.5 M in Et2O, 22.4 mL, 11.2 mmol) stirred under nitrogen atmosphere and the mixture was further stirred at RT for 24 h. The reaction mixture was diluted with EtOAc, and washed with a saturated aqueous solution of NaHCO3, then with water. The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 94:6 to c-hexane/EtOAc 8:2) to give the desired material. TLC, Rf (c-hexane/EtOAc 4:1)=0.3; MS (UPLC): 232.2 [M+H]+, 176.1 [MH−tBu]+, 249.2 [M+NH4]+, 463.4 [2M+H]+, 273.3 [M+HCOO]−.

Workup

  1. stirringthe mixture was further stirred at RT for 24 h
  2. washwashed with a saturated aqueous solution of NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 94:6 to c-hexane/EtOAc 8:2)

Sources & evidence

ORD record
ord-f1f7efc7cae64cf9afe9a7c7418c5fdf
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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