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

HRID 1836630Notes

Reaction equation

HRID 1836630 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): δ9.84 (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-d1ceae8de2724fa3833132048698e63e
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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