Potassium Phosphate, Tribasic → HCID 136377276, compound

HRID 2274466Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH2:27][CH3:28])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[C:12]1[N:13]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:14]=[CH:15][N:16]=1)=[CH:8][CH:7]=[C:6](Cl)[N:5]=2.[Cl:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[OH:36].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.O1CCOCC1.O>[NH2:1][C:2]1[N:3]([CH2:27][CH3:28])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[C:12]1[N:13]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[CH:14]=[CH:15][N:16]=1)=[CH:8][CH:7]=[C:6]([C:32]1[CH:33]=[CH:34][C:35]([OH:36])=[C:30]([Cl:29])[CH:31]=1)[N:5]=2

Participants

Conditions

Temperature: 85 °C

Procedure

In a round bottom flask 0.3 g (0.71 mmol) 2-amino-7-chloro-1-ethyl-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-1H-[1,8]naphthyridin-4-one, 0.185 g (1.07 mmol) 3-chloro-4-hydroxy-phenylboronic acid, 0.098 g (0.11 mmol) tris-(dibenzylidenacetone)dipalladium (0), 0.030 mg (0.0.11 mmol) tricyclohexyl phosphine, 0.303 g of potassium phosphate tribasic, and 8 mL of dioxane/water (50/50) (degassed) were stirred and heated at 85° C. for 8 h. The solvents were evaporated and the residue was purified by column chromatography (DCM/MeOH: 9/1) to yield 0.4 g of a brown solid. This solid was engaged without further purification in the next step.

Workup

customThe solvents were evaporated
customthe residue was purified by column chromatography (DCM/MeOH: 9/1)

Sources & evidence

ORD record: ord-0af23d10428d42aaa277cfe093222013
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126972B2

Reaction notes

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