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

HRID 448577Notes

Reaction equation

HRID 448577 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([N:21]3[C:29]4[C:24](=[CH:25][C:26]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:27][CH:28]=4)[CH2:23][CH2:22]3)[N:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:44])(=O)=O)=CC=1>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[C:20]([F:44])=[C:19]([N:21]3[C:29]4[C:24](=[CH:25][C:26]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:27][CH:28]=4)[CH2:23][CH2:22]3)[N:18]=[CH:17][N:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 588007N-FluorobenzenesulfonimideHCID 25242414Tert-butyl 4-((6-(5-(methylsulfonyl)indolin-1-yl)pyrimidin-4-yl)oxy)piperidine-1-carboxylate

Product 1

HCID 581166014-[5-Fluoro-6-(5-methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

4a (43 mg, 0.09 mmol) was dissolved in 1 mL of DCE with N-fluorobenzenesulfonimide (62 mg, 0.2 mmol). The mixture was stirred for 2 days at 75° C. then the solvent was evaporated under vacuum. The crude material was dissolved in 20% of DCM in methanol and purified by preparative HPLC to give 13-1; LCMS 493.1 (MH+), tR=5.21 (Method 5). EC50: 382 nM.

Workup

  1. customthe solvent was evaporated under vacuum
  2. dissolutionThe crude material was dissolved in 20% of DCM in methanol
  3. custompurified by preparative HPLC
  4. customto give 13-1

Sources & evidence

ORD record
ord-d2ad9ba67206444c98b729700748fb95
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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