Triethylamine → 6-Benzyloxy-3-(5-ethoxy-3-isoxazolyl)-4-methoxymethyl-beta-carboline

HRID 2107055Notes

Reaction equation

HRID 2107055 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH:16]=[N:15][C:14]([CH:22]=[N:23][OH:24])=[C:13]([CH2:25][O:26][CH3:27])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O.[CH2:36]([O:38][C:39]#[CH:40])[CH3:37].C(N(CC)CC)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH:16]=[N:15][C:14]([C:22]3[CH:37]=[C:36]([O:38][CH2:39][CH3:40])[O:24][N:23]=3)=[C:13]([CH2:25][O:26][CH3:27])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61239Ether, ethyl ethynylHCID 67184N-bromobutanimideHCID 1363646136-Benzyloxy-4-methoxymethyl-beta-carboline-3-carbaldehyde Oxime

Product 1

HCID 143729376-Benzyloxy-3-(5-ethoxy-3-isoxazolyl)-4-methoxymethyl-beta-carboline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.1 g (3.0 mmol) of 6-benzyloxy-4-methoxymethyl-β-carboline-3-carbaldehyde oxime is dissolved in 40 ml of dry DMF and combined with 0.56 g (3.1 mmol) of N-bromosuccinimide (dissolved in 5 ml of DMF). The reaction mixture is stirred for 15 minutes at room temperature and then combined with 1.5 eq. of ethoxyacetylene and 2 ml of triethylamine. The reaction mixture is agitated overnight at room temperature, then poured on ice water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered, the solvent drawn off, and the residue purified by column chromatography on silica gel with ethyl acetate. Melting point: 139°-140° C.

Workup

  1. stirringThe reaction mixture is agitated overnight at room temperature
  2. additionpoured on ice water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe residue purified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-9baeed1e3cf2474d97dbce14c472ab09
Source dataset
uspto-grants-1990_06
Patent number
US04933345

Reaction notes

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