Water → HCID 136061484, compound

HRID 2245232Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>C1(C)C=CC=CC=1.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:8][C:4]1[CH:3]=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[CH:7]=[CH:6][N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Bromo-2-chloropyridine (310 mg, 1.6 mmol), 531 mg (2.4 mmol) of 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol, 10.8 mg (0.016 mmol) of Pd(OAc)2, 710 mg (3.3 mmol) of K3PO4 and Xantphos[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene] (18.6 mg, 0.032 mmol) in toluene: water (5:0.5 mL) were sealed in a microwave vessel and heated by microwave irradiation at 100° C. for 2 minutes. The reaction mixture was cooled and diluted with 10 mL of CH2Cl2, washed with water (5 mL), dried over Na2SO4, and evaporated under reduced pressure. The residue was dissolved in DMSO and purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give 5a. LC/MS: m/z 206.1 (m+H)+, r.t (retention time)=2.86 min (10%-99% CH3CN (0.035% TFA)H2O (0.05% TFA) to give 5.

Workup

temperatureThe reaction mixture was cooled
washwashed with water (5 mL)
dry with materialdried over Na2SO4
customevaporated under reduced pressure
dissolutionThe residue was dissolved in DMSO
custompurified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)

Sources & evidence

ORD record: ord-9088f56e66d54fd89353be9a4096777a
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683065B2

Reaction notes

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