Dimethylformamide → N,N-dimethyl-2-(3-formyl-indol-5-yl)cycloprop-1-yl-methylamine

HRID 2416253Notes

Reaction equation

HRID 2416253 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH2:9][CH:10]1[CH2:12][CH:11]1[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2)[CH3:8].[OH-].[Na+].CN([CH:27]=[O:28])C>O>[CH3:8][N:7]([CH2:9][CH:10]1[CH2:12][CH:11]1[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[CH:27]=[O:28])[CH3:6]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 67550440N,N-dimethyl-2-(indol-5-yl)cycloprop-1-yl-methylamine

Product 1

HCID 22638743N,N-dimethyl-2-(3-formyl-indol-5-yl)cycloprop-1-yl-methylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorous oxychloride (0.08 mL, 0.85 mmol, 0.91 equiv.) and dimethyl formamide (0.32 mL, 4.09 mmol, 4.4 equiv.) were combined at room temperature with stirring. After 15 min, N,N-dimethyl-2-(indol-5-yl)cycloprop-1-yl-methylamine was added dropwise in DMF (5 mL). After 2 hs of stirring at room temperature, ice and 1 N NaOH were added, then the mixture was diluted further with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give N,N-dimethyl-2-(3-formyl-indol-5-yl)cycloprop-1-yl-methylamine (120 mg) as an oil. 1H NMR (MeOH-d4): δ 9.84 (s, 1H), 8.04 (s, 1H), 7.97 (s, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.05 (dd, J=15.5, 1.7 Hz, 1H), 2.59 (dd, J=12.7, 6.7, 1H), 2.35 (s, 6H), 2.30 (m, 1H), 1.80 (m, 1H), 1.20 (m, 1H), 1.05 (m, 1H), and 0.88 (m, 1H).

Workup

  1. customwere combined at room temperature
  2. stirringAfter 2 hs of stirring at room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd884391c511400c89438750fc9e9439
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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