5-Bromoindoline → 4-[6-(5-Bromo-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

HRID 448559Notes

Reaction equation

HRID 448559 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.CC(C)([O-])C.[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:30][C:31]2[CH:36]=[C:35](Cl)[N:34]=[CH:33][N:32]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCOCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:30][C:31]2[CH:36]=[C:35]([N:7]3[C:8]4[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=4)[CH2:5][CH2:6]3)[N:34]=[CH:33][N:32]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 34115665-BromoindolineHCID 21906116tert-Butyl 4-[(6-chloropyrimidin-4-yl)oxy]piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 668941954-[6-(5-Bromo-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromoindoline (60 mg, 0.3 mmol) and potassium tert-butoxide (0.1 g, 3 eq) were stirred for 5 minutes in dioxane (1 mL). 3a (0.1 g, 1.05 eq) was added and the mixture was stirred at 80° C. for 72 h. The solvent was removed under vacuum and the residue was dissolved in THF and purified by preparative HPLC to give 3b.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in THF
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-07e99a8729f849cca13a40a5dd12ace7
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

Loading…