Potassium Carbonate → 1-(5-(7-Chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-cycloheptylurea

HRID 715135Notes

Reaction equation

[CH:1]1([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:15]=[CH:14][C:13]=2[F:27])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)S(O[C:34]1[C:35]([CH3:45])=[N:36][C:37]2[C:42]([CH:43]=1)=[CH:41][N:40]=[C:39]([Cl:44])[CH:38]=2)(=O)=O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:44][C:39]1[CH:38]=[C:37]2[C:42]([CH:43]=[C:34]([C:16]3[CH:15]=[CH:14][C:13]([F:27])=[C:12]([NH:11][C:9]([NH:8][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]4)=[O:10])[CH:17]=3)[C:35]([CH3:45])=[N:36]2)=[CH:41][N:40]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sparge a suspension of 1-cycloheptyl-3-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (0.420 g, 1.116 mmol), 7-chloro-2-methyl-1,6-naphthyridin-3-yl trifluoromethanesulfonate (0.438 g, 1.339 mmol) and K2CO3 (0.463 g, 3.35 mmol) in dioxane (4 mL) and H2O (1 mL) with Ar, add Pd(PPh3)4 (0.064 g, 0.056 mmol) and heat at 60° C. for 3 h. Concentrate the mixture to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (679 mg, 61%) as a white solid. MS(ESI) m/z: 427.1 (M+H+).

Workup

customSparge
concentrationConcentrate the mixture to dryness
custompurify via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record: ord-f39e90d8b00b4d10a21b877cacfe20be
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187474B2

Reaction notes

Loading…