Dichloromethane → HCID 44224441, compound

HRID 1907843Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[C:6]=2[N:7]=1.[CH3:22][N:23]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[N:24]1.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>COCCOC.O>[CH3:22][N:23]1[CH:27]=[C:26]([C:2]2[N:3]=[CH:4][C:5]3[N:10]=[N:9][N:8]([CH2:11][C:12]4[CH:13]=[C:14]5[C:19](=[CH:20][CH:21]=4)[N:18]=[CH:17][CH:16]=[CH:15]5)[C:6]=3[N:7]=2)[CH:25]=[N:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-((5-chloro-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)methyl)quinoline (393 mg, 1.33 mmol) in DME (8 mL) was added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (415 mg, 1.99 mmol) and Cs2CO3 (1.30 g, 3.98 mmol) in H2O (1.3 mL). The reaction mixture was degassed twice. The palladium catalyst Pd(dppf).CH2Cl2 (63 mg, 0.077 mmol) was added and the reaction mixture was degassed for two more times, and heated to 80° C. for 15 h under nitrogen. After cooling to room temperature, the solvent was removed under reduced pressure. Flash chromatography of the residue over silica gel, using 50% hexane in EtOAc to 100% EtOAc to 10% MeOH in EtOAc, gave the desired product (130 mg, 29%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 4.00 (s, 3H), 6.04 (s, 2H), 7.39-8.29 (m, 7H), 8.92 (m, 1H), 9.44 (s, 1H); LCMS (APCI) m/z 343.0 (M+H+).

Workup

customThe reaction mixture was degassed twice
customthe reaction mixture was degassed for two more times
temperatureAfter cooling to room temperature
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-111c9079ede442bab1158e132a7fe98d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598184B2

Reaction notes

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