Propargyl bromide → 3-(5-bromomethyl-isoxazol-3-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole

HRID 644070Notes

Reaction equation

HRID 644070 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([CH:19]=[N:20][OH:21])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClN1C(=O)CCC1=O.[CH2:30]([Br:33])[C:31]#[CH:32].C(N(CC)CC)C>ClCCl>[Br:33][CH2:30][C:31]1[O:21][N:20]=[C:19]([C:10]2[C:11]3[C:16](=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:9]=2)[CH:32]=1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 860732891-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime

Product 1

HCID 686958133-(5-bromomethyl-isoxazol-3-yl)-1-cyclohexylmethyl-7-methoxy-1H-indoleYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime (170 mg, 0.59 mmol) in dichloromethane (5 ml) cooled to 0° C., was added N-chlorosuccinimide (119 mg, 0.89 mmol) and the mixture allowed to warm to room temperature with stirring for 1 h. Propargyl bromide (8 μl, 0.65 mmol) and triethylamine (9 μl, 0.65 mmol) were added and the mixture stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography eluting with 60-80% (v/v) dichloromethane in n-heptane to afford 3-(5-bromomethyl-isoxazol-3-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (150 mg, 0.37 mmol) as a yellow solid.

Workup

  1. stirringthe mixture stirred at room temperature for 16 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash column chromatography
  4. washeluting with 60-80% (v/v) dichloromethane in n-heptane

Sources & evidence

ORD record
ord-e8b71b51163d404eada7a98bb40cf3f7
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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