Dimethylformamide → HCID 72192144, compound

HRID 2174047Notes

Reaction equation

HRID 2174047 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:22])[C:5](I)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.CN([CH:26]=[O:27])C.C([Li])CCC>COC1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=2[C:5]([CH:26]=[O:27])=[C:4]([CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 867016707-chloro-4-iodo-5-methyl-1-tosyl-1H-indoleHCID 178418339Butyllithium2×

Product 1

HCID 72192144HCID 72192144, compound

Reagents, catalysts & solvents 1

HCID 138539Cyclopentyl methyl etherSolvent

Procedure

To a solution of 7-chloro-4-iodo-5-methyl-1-tosyl-1H-indole (98 mg, 0.220 mmol) and DMF (34 μL, 0.440 mmol) in cyclopentyl methyl ether (2 mL) at −78° C., was added n-butyllithium (2.5 M in hexanes, 114 μL, 0.286 mmol). After 80 minutes additional n-butyllithium (2.5 M in hexanes, 0.11 mL, 0.286 mmol) was added. After 15 more minutes the reaction was quenched with MeOH (0.5 mL) and sat. aq. NH4Cl. The layers were separated and the aqueous layer was extracted with EtOAc, washed with brine, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 347.9 (M+H).

Workup

  1. customAfter 15 more minutes the reaction was quenched with MeOH (0.5 mL) and sat. aq. NH4Cl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes)

Sources & evidence

ORD record
ord-f2214282ced7411fb3572f6b48f2e8c1
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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