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Ammonium Chloride → 1-(5,7-Dimethyl-1-tosyl-1H-indol-4-yl)prop-2-en-1-one

HRID 2174021
Notes
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Reaction equation

HRID 2174021 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:22]=[O:23].[CH:24]([Mg]Br)=[CH2:25].[NH4+].[Cl-].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1.O>[CH3:1][C:2]1[C:3]([C:22](=[O:23])[CH:24]=[CH2:25])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 159087TriacetoxyperiodinaneHCID 86701532HCID 86701532, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 867016201-(5,7-Dimethyl-1-tosyl-1H-indol-4-yl)prop-2-en-1-one

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (Example 46-D) (500 mg, 1.53 mmol) in THF (15 mL) at −78° C., vinylmagnesium bromide (2.29 mL, 2.29 mmol) was added and the reaction was stirred for 15 minutes. At this point a saturated water solution of NH4Cl was added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over MgSO4 and evaporated. The resulting residue was dissolved in DCM (4 mL), and Dess-Martin Periodinane (1.19 g, 2.81 mmol) was added. After 15 minutes the reaction was complete. The reaction was quenched with a sat. aq. solution of NaHCO3 and sodium thiosulfate. The layers were separated and the aqueous layer was extracted with DCM. It was purified using FCC eluting with heptane/EtOAc 1:1 to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=3.79 Hz, 1H), 7.50-7.66 (m, J=8.34 Hz, 2H), 7.30-7.45 (m, J=8.34 Hz, 2H), 7.01 (s, 1H), 6.71 (dd, J=10.48, 17.56 Hz, 1H), 6.59 (d, J=4.04 Hz, 1H), 6.14 (d, J=10.86 Hz, 1H), 5.88 (d, J=17.43 Hz, 1H), 2.35 (s, 3H), 2.21 (s, 3H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organics were dried over MgSO4
  4. customevaporated
  5. dissolutionThe resulting residue was dissolved in DCM (4 mL)
  6. waitAfter 15 minutes the reaction was complete
  7. customThe reaction was quenched with a sat. aq. solution of NaHCO3 and sodium thiosulfate
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with DCM
  10. customIt was purified
  11. washeluting with heptane/EtOAc 1:1

Sources & evidence

ORD record
ord-2499bb690c0f43cb9485867c50a18db7
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056874B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes