Potassium Carbonate → HCID 71525433, compound

HRID 1755286Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)O1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:4]2[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=[C:2]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:3]=2)=[N:13][CH:14]=1)[CH3:19]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-chloro-N-(5-ethylpyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (329 mg, 1.21 mmol), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (221 mg, 1.81 mmol), Pd2(dba)3 (70 mg, 0.121 mmol), X-Phos (231 mg, 0.484 mmol) and K2CO3 (499 mg, 3.62 mmol) in dioxane (40 mL) and H2O (10 mL) was heated to 110° C. for 20 h under N2. The mixture was cooled and concentrated in vacuo. The residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:5) to afford N-(5-ethylpyridin-2-yl)-6-phenylimidazo[1,2-b]pyridazin-8-amine (84 mg, 22%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.69 (s, 1H), 8.37 (d, 1H, J=1.8 Hz), 8.24 (s, 1H), 8.09-8.01 (m, 3H), 7.68-7.55 (m, 5H), 7.02 (d, 1H, J=8.4 Hz), 2.75 (q, 2H, J=7.8 Hz), 1.37 (t, 3H, J=7.8 Hz). LC-MS: 316, [M+H]+, tR=1.827 min, HPLC: 99.73% at 214 nm, 99.88% at 254 nm, tR=3.262 min.

Workup

temperatureThe mixture was cooled
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:5)

Sources & evidence

ORD record: ord-d176395b16a3411fa74d96144c75423b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169259B2

Reaction notes

Loading…