Potassium tert-butoxide → 6-(3-chloro-2-fluorobenzyl)-2-((3-fluorobenzyl)oxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533147Notes

Reaction equation

HRID 533147 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[NH:12][CH2:11][CH2:10][C:9]=2[N:8]=1.[F:21][C:22]1[C:23]([Cl:30])=[C:24]([CH:27]=[CH:28][CH:29]=1)CBr.[CH3:31]C([O-])(C)C.[K+]>CS(C)=O>[Cl:30][C:23]1[C:22]([F:21])=[C:29]([CH:28]=[CH:27][CH:24]=1)[CH2:31][N:12]1[CH2:11][CH2:10][C:9]2[N:8]=[C:7]([O:6][CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=3)[CH:16]=[CH:15][C:14]=2[C:13]1=[O:17]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 447826441-(Bromomethyl)-2-chloro-3-fluorobenzeneHCID 574052642-((3-fluorobenzyl)oxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Product 1

HCID 680075986-(3-chloro-2-fluorobenzyl)-2-((3-fluorobenzyl)oxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-((3-fluorobenzyl)oxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (20 mg, 0.05 mmol, prepared above as in Example 1.1) in DMSO (1 mL) was treated with 3-fluoro-2-chlorobenzyl bromide (20 mg 0.12 mmol) and KOtBu (20 mg, 0.18 mmol). The reaction mixture was stirred at RT overnight and then purified directly by RP-HPLC to give indicated compound. LC-MS (M+H)=415.3.

Workup

  1. custompurified directly by RP-HPLC
  2. customto give

Sources & evidence

ORD record
ord-6b24a47449dc4c3580d74a7f258d13eb
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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