Dimethylformamide → HCID 86701532, compound

HRID 2173964Notes

Reaction equation

HRID 2173964 reaction equation
I[C:2]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].CN([CH:26]=[O:27])C.CCCCCC>COC1CCCC1.C([Li])CCC>[CH3:11][C:10]1[CH:9]=[C:8]([CH3:12])[C:7]2[N:6]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]=2[C:2]=1[CH:26]=[O:27]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8058Hexane2×HCID 867015334-iodo-5,7-dimethyl-1-tosyl-1H-indole

Product 1

HCID 86701532HCID 86701532, compound

Reagents, catalysts & solvents 2

HCID 138539Cyclopentyl methyl etherSolventHCID 178418339ButyllithiumSolvent2×

Procedure

To a solution of 4-iodo-5,7-dimethyl-1-tosyl-1H-indole (950 mg, 2.1 mmol) and DMF (0.33 mL, 4.2 mmol) in cyclopentyl methyl ether (22 mL), n-butyllithium in hexane (2.2 M, 1.3 mL, 2.8 mmol) was added at −78° C. After stirring for 1 h, additional n-butyllithium in hexane (2.2 M, 0.19 mL, 0.42 mmol) was added. After stirring for 15 min, the reaction was quenched with MeOH (2 mL) and 1M aq. NaHSO4 (4.5 mL), and diluted with EtOAc and brine. The layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, washed with brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave a residue that was purified by FCC [(10% DCM/heptane)/(20% EtOAc/DCM)=100/0 to 50/50] to give the title compound. MS (ESI+) m/z 328.2 (M+H).

Workup

  1. stirringAfter stirring for 15 min
  2. customthe reaction was quenched with MeOH (2 mL) and 1M aq. NaHSO4 (4.5 mL)
  3. additiondiluted with EtOAc and brine
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customConcentration of the filtrate gave a residue that
  10. customwas purified by FCC [(10% DCM/heptane)/(20% EtOAc/DCM)=100/0 to 50/50]

Sources & evidence

ORD record
ord-9793d562238e4e93839b9b55e91a72d7
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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