1,2-Dibromoethane → HCID 86675603, compound

HRID 1465729Notes

Reaction equation

HRID 1465729 reaction equation
C[N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[C:3]1CN(C)CC#C.[Br:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:18][CH2:19][CH2:20][O:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:2][CH:3]=[CH:4]2

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 3035581N-Methyl-N-(2-propynyl)-2-(5-hydroxy-1-methylindolyl)methylamine

Product 1

HCID 86675603HCID 86675603, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 1-methyl-2-{[methyl(prop-2-yn-1-yl)amino]methyl}-1H-indol-5-ol (8) (Cruces, M. A.; Elorriaga, C.; Fernández-Álvarez, E. Eur. J. Med. Chem. 1991, 26, 33-41) (0.215 g, 0.942 mmol), 1,2-dibromoethane (1.77 g, 9.42 mmol), and potassium carbonate (0.65 g, 4.71 mmol) in 2-butanone (8 mL) was heated at 85° C. for 6 h. The mixture was evaporated under vacuum and the residue was extracted with dichloromethane (10 mL) and water (10 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by column chromatography, eluting with a 4% methanol mixture in dichloromethane to give compound 9 (117.3 mg, 37%). Rf=0.76 (CH2Cl2/AcOEt, 10/1); pf 75-77° C.; RMN of 1H (300 MHz, CDCl3) δ 2.31 (t, J=2.4 Hz, 1H, ≡CH), 2.36 (s, 3H, N—CH3), 3.32 (d, J=2.4 Hz, 2H, N—CH2—C≡), 3.66 (t, J=6.4 Hz, 2H, —CH2—Br), 3.69 (s, 2H, N—CH2), 3.75 (s, 3H, N—CH3), 4.33 (t, J=6.4 Hz, 2H, —CH2—O—), 6.36 (s, 1H, CH3), 6.9 (dd, J=8.8, 2.5 Hz, 1H, CH6), 7.07 (d, J=2.4 Hz, 1H, CH4), 7.2 (d, J=8.8 Hz, 1H, CH7); RMN of 13C (75 MHz, CDCl3) δ 29.6 (CH2—Br), 29.9 (N—CH3), 41.5 (N—CH3), 44.7 (—CH2—C≡), 51.7 (CH2—N), 69.1 (CH2—O), 73.5 (≡CH), 78.3 (—C≡), 102.15 (CH3ind), 104.42 (CH4ind), 109.7 (CH7ind), 112.2 (CH6ind), 127.4 (C3aind), 133.8 (C7aind), 137.3 (C2ind), 152.2 (C5ind); EM (IE) m/z (%): 131 (48), 160 (66) [M-((Br(CH2)2)—NCH3CH2C≡CH)]+, 267 (100) [M-NCH3CH2C≡CH)]+, 334 (25)[M]+

Workup

  1. customThe mixture was evaporated under vacuum
  2. extractionthe residue was extracted with dichloromethane (10 mL) and water (10 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with a 4% methanol mixture in dichloromethane

Sources & evidence

ORD record
ord-31a3700ae95147df8607d5086a82a7a2
Source dataset
uspto-grants-2015_04
Patent number
US08999994B2

Reaction notes

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