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

HRID 2416252Notes

Reaction equation

HRID 2416252 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): δ 7.26 (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-676ea6f8028e43739edb9e63b5abe127
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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