Potassium Hydroxide → HCID 58065873, compound

HRID 1752208Notes

Reaction equation

HRID 1752208 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+].[O:24]([CH2:31][CH:32]1[CH2:34][O:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:34][CH:32]([OH:33])[CH2:31][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:6]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 31217Phenyl glycidyl etherHCID 57950382tert-Butyl 8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 58065873HCID 58065873, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 8-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (449.7 mg, 1.28 mmol) and powdered potassium hydroxide (86.9 mg, 1.54 mmol) in acetone (4.0 ml) was stirred for 15 minutes before the addition of 2-(phenoxymethyl)oxirane (254 mg, 1.69 mmol). After 1 h the reaction was condensed, diluted with EtOAc and washed twice with water and then brine. The organic layer was then dried over Na2SO4, filtered and condensed. The crude mixture was purified by silica gel chromatography (1% MeOH/CH2Cl2+0.1% Et3N). Yield=21%. ESI (m/z): 546.6 (M+CHCOO−).

Workup

  1. customcondensed
  2. washwashed twice with water
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. filtrationfiltered
  5. customcondensed
  6. customThe crude mixture was purified by silica gel chromatography (1% MeOH/CH2Cl2+0.1% Et3N)

Sources & evidence

ORD record
ord-ab7c1051e931418e8ff30a83c5ea515c
Source dataset
uspto-grants-2015_10
Patent number
US09162980B2

Reaction notes

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