Sodium Bicarbonate → HCID 53344959, compound

HRID 1404296Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:12]=2)[CH:7]=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([F:40])=[C:25]([C:27]2[CH:36]=[C:35](B(O)O)[C:34]3[C:29](=[N:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)[CH:26]=1.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:20][C:21]1[CH:22]=[CH:23][C:24]([F:40])=[C:25]([C:27]2[CH:36]=[C:35]([C:2]3[CH:3]=[N:4][CH:5]=[C:6]([C:8]4[CH:9]=[N:10][N:11]([CH2:13][CH2:14][N:15]5[CH2:19][CH2:18][CH2:17][CH2:16]5)[CH:12]=4)[CH:7]=3)[C:34]3[C:29](=[N:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)[CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A slurry of 161 mg (0.50 mmol) 3-bromo-5-[1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-pyridine, 167 mg (0.55 mmol) 2-(5-Chloro-2-fluoro-phenyl)-[1,8]naphthyridine-4-boronic acid and 50.4 mg (0.6 mmol) sodium bicarbonate in 2 ml DMF and 0.5 ml water was heated at 80° C. under nitrogen. Then 7.0 mg (0.01 mmol) bis-(triphenylphosphine)-palladium(II)-chloride were added. The reaction mixture was stirred for 40 hours at 80° C. Water was added, the resulting precipitate was filtered off and washed with water. The residue was chromatographed on a silica gel column with dichloromethane/methanol as eluent yielding 2-(5-Chloro-2-fluoro-phenyl)-4-{5-[1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-pyridin-3-yl}-[1,8]naphthyridine as colourless crystals; HPLC-MS: 1.67 min, [M+H] 499.

Workup

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

Sources & evidence

ORD record: ord-d888ce6258304c2caaa7dfa37b8b8c42
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912216B2

Reaction notes

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