HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium tert-butoxide → Methyl 5-nitro-2-[3-(tetrahydropyran-2-yloxy)-propyl]-1H-indole-4-carboxylate

HRID 715959
Notes
Print preview

Reaction equation

HRID 715959 reaction equation
CC(C)([O-])C.[K+].C([NH:10][C:11]1[C:12]([C:24]#[C:25][CH2:26][CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)=[C:13]([C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])(=O)C>CN1CCCC1=O.C(OCC)(=O)C>[N+:21]([C:18]1[CH:19]=[CH:20][C:11]2[NH:10][C:25]([CH2:26][CH2:27][CH2:28][O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)=[CH:24][C:12]=2[C:13]=1[C:14]([O:16][CH3:17])=[O:15])([O-:23])=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 70983837Methyl 3-acetylamino-6-nitro-2-[5-(tetrahydropyran-2-yloxy)-pent-1-ynyl]benzoate2×

Product 1

HCID 70983448Methyl 5-nitro-2-[3-(tetrahydropyran-2-yloxy)-propyl]-1H-indole-4-carboxylateYield 84.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
70 °C

Procedure

Potassium tert-butoxide (0.230 g) was added to a solution of methyl 3-acetylamino-6-nitro-2-[5-(tetrahydropyran-2-yloxy)-pent-1-ynyl]benzoate (Intermediate 23, 0.70 g) in anhydrous N-methyl-2-pyrrolidone (18 mL) and the reaction mixture was heated at 70° C. for 1 hour. After cooling, the mixture was diluted with ethyl acetate, washed with water and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 5-nitro-2-[3-(tetrahydropyran-2-yloxy)-propyl]-1H-indole-4-carboxylate (0.530 g) as a dark orange gum.

Workup

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c273724d37e14bbda0ff8eac1d3a495a
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187494B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes