Triethylamine → 6-Bromo-3-(3-isoxazolyl)-beta-carboline

HRID 2107057Notes

Reaction equation

HRID 2107057 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([CH:14]=[N:15][OH:16])[N:2]=1.[Br:17]N1C(=O)CCC1=O.C[Si]([C:29]#[CH:30])(C)C.C(N(CC)CC)C>C1COCC1>[Br:17][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[NH:12][C:13]1[CH:1]=[N:2][C:3]([C:14]3[CH:30]=[CH:29][O:16][N:15]=3)=[CH:4][C:5]2=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 67184N-bromobutanimideHCID 1363992769H-pyrido[3,4-b]indole-3-carboxaldehyde oxime

Product 1

HCID 143729496-Bromo-3-(3-isoxazolyl)-beta-carboline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.05 g (5 mmol) of β-carboline-3-carbaldehyde oxime is suspended in 50 ml of dry THF and combined at 0° C. with 1.8 g of N-bromosuccinimide in 20 ml of dry THF. The reaction mixture is heated to room temperature, stirred for 95 hours, and combined with 1.5 eq. of trimethylsilylacetylene and 2 ml of triethylamine. The mixture is further stirred overnight, poured on ice water, and extracted with ether. The organic phase is dried over magnesium sulfate, filtered, and the solvent drawn off. The remaining oil is dissolved in 10 ml of DMF and combined with 10 ml of sodium hydroxide solution (1-molar). The reaction mixture is stirred overnight at room temperature, poured on water, and extracted with ethyl acetate. The resultant product is purified by column chromatography with ethyl acetate as the eluent. Melting point: 292°-293° C.

Workup

  1. waitThe mixture is further stirred overnight
  2. additionpoured on ice water
  3. extractionextracted with ether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. dissolutionThe remaining oil is dissolved in 10 ml of DMF
  7. stirringThe reaction mixture is stirred overnight at room temperature
  8. additionpoured on water
  9. extractionextracted with ethyl acetate
  10. customThe resultant product is purified by column chromatography with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-2523b53ef10a439f926a3d0b327b4181
Source dataset
uspto-grants-1990_06
Patent number
US04933345

Reaction notes

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