Water → HCID 86685973, compound

HRID 2277679Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH2:19]Cl)[CH:18]=1)[CH2:6][CH2:5]2.C([O-])([O-])=O.[Na+].[Na+].[CH3:27][C:28]1[C:32](B(O)O)=[C:31]([CH3:36])[O:30][N:29]=1.O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH2:19][C:32]3[C:28]([CH3:27])=[N:29][O:30][C:31]=3[CH3:36])[CH:18]=1)[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 120 °C

Procedure

6-Chloro-2-(5-chloromethyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (example 140 [A]) (75 mg, 0.25 mmol), Pd(PPh3)2Cl2 (18 mg, 0.025 mmol), Na2CO3 (80 mg, 0.75 mmol) and 3,5-dimethylisoxazole-4-boronic acid (45 mg, 0.32 mmol) were dissolved in dioxane (4.0 mL). The resulting reaction mixture was heated at 120° C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×125 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by prep-HPLC to give title compound (10 mg, 10.9%) as a light yellowish solid. MS: 368.2 (M+H+).

Workup

customThe resulting reaction mixture
extractionextracted with EtOAc (2×125 mL)
washThe combined organic layers were washed with brine
customdried over anhy
filtrationNa2SO4, filtered
concentrationconcentrated in vacuo
customto give a crude product which
customwas then purified by prep-HPLC

Sources & evidence

ORD record: ord-c5280ba029a34810a68844cff341a2c3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133158B2

Reaction notes

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