Sodium Bicarbonate → 2-(4-Chloro-[1,8]naphthyridin-2-yl)-benzamide

HRID 1404283Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O)#[N:14].C(=O)(O)[O-:25].[Na+]>CN(C=O)C.O>[Cl:12][C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:13]([NH2:14])=[O:25])[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 1.99 g (10.0 mmol) 2,4-dichloro-[1,8]naphthyridine, 1.47 g (10.0 mmol) 2-cyanobenzeneboronic acid and 1.01 g (120.0 mmol) sodium bicarbonate in 100 ml DMF and 50 ml water was heated to 80° C. under nitrogen. 140 mg (0.20 mmol) bis-(triphenyl-phosphine)-palladium(II)-chloride were added and the mixture was stirred for 16 hrs at 80° C. Water was added to the reaction mixture and the resulting precipitate was filtered off and washed well with water. The residue was dried in vacuum yielding 2-(4-chloro-[1,8]naphthyridin-2-yl)-benzamide as yellow crystals; HPLC-MS: 1.55 min, [M+H] 284.

Workup

filtrationthe resulting precipitate was filtered off
washwashed well with water
customThe residue was dried in vacuum

Sources & evidence

ORD record: ord-7cac15b8af884bb3b7b01a49abe722d3
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912216B2

Reaction notes

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