Sodium Bicarbonate → HCID 56591567, compound

HRID 1629913Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C:8]2[CH:17]=[C:16](B(O)O)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1.Br[C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][N:27]=[CH:28]2.C(=O)(O)[O-].[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C:8]2[CH:17]=[C:16]([C:23]3[CH:32]=[CH:31][CH:30]=[C:29]4[C:24]=3[CH:25]=[CH:26][N:27]=[CH:28]4)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A slurry of 151 mg (0.50 mmol) 2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridine-4-boronic acid, 84.9 mg (0.40 mmol) 5-bromoisoquinoline and 44.4 mg (0.53 mmol) sodium bicarbonate in 2 ml DMF and 1 ml water was heated to 80° C. under nitrogen. Then 16.3 mg (0.02 mmol) bis-(triphenylphosphine)-palladium(II)-chloride were added. The reaction mixture was stirred for 18 hours at 80° C. Water was then added to the reaction mixture and the resulting precipitate was filtered off. The residue was chromatographed on a silica gel column with dichloromethane/methanol as eluent yielding 2-(5-chloro-2-fluoro-phenyl)-4-isoquinolin-5-yl-[1,8]naphthyridine as colourless crystals: HPLC/MS: 2.10 min, [M+H] 386.

Workup

filtrationthe resulting precipitate was filtered off
customThe residue was chromatographed on a silica gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record: ord-fd9b8a57aae3486bb335bd783e5ee2cb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791113B2

Reaction notes

Loading…