Cyanogen Bromide → N,N-dimethyl-2-(3-bromoindol-5-yl)cycloprop-1-yl methylamine

HRID 1836629Notes

Reaction equation

HRID 1836629 reaction equation
[CH3:1][N:2]([CH2:4][C@@H:5]1[CH2:7][C@H:6]1[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)[CH3:3].CC(C)([O-])C.[K+].N#C[Br:25]>C1COCC1>[CH3:3][N:2]([CH2:4][CH:5]1[CH2:7][CH:6]1[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[Br:25])[CH3:1]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 23665647Potassium tert-butoxideHCID 71612687trans N,N-dimethyl-2-(indol-5-yl)cycloprop-1-yl methylamine

Product 1

HCID 23518952N,N-dimethyl-2-(3-bromoindol-5-yl)cycloprop-1-yl methylamineYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans N,N-dimethyl-2-(indol-5-yl)cycloprop-1-yl methylamine (75 mg, 0.35 mmol), and potassium t-butoxide (29 mg, 0.35 mmol) in anhydrous THF at 0° C. was stirred at 0° C. for 30 min before cyanogen bromide (37 mg, 0.35 mmol) was added. The reaction was warmed to room temperature and stirred for 16 h. The reaction was concentrated in vacuo, and the residue was dissolved in water, and extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give N,N-dimethyl-2-(3-bromoindol-5-yl)cycloprop-1-yl methylamine (100 mg, 98%) as a colorless oil. 1H NMR (MeOH-d4): δ7.26 (d, J=8.4 Hz, 1H), 7.22 (s, 1H), 7.16 (s, 1H), 6.94 (dd, J=8.7, 1.5 Hz, 1H), 2.58 (dd, J=6.0, 1H), 2.35 (s, 6H), 2.31 (m, 1H), 1.80 (m, 1H), 1.22 (m, 1H), 1.03 (m, 1H), and 0.88 (m, 1H). FIMS: 293.1 (M−H), reverse-phase HPLC purity: 85%.

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fe107066a234b50b540dec4ad43c0ed
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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