Potassium Carbonate → HCID 67974368, compound

HRID 468742Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)=[CH:6][C:5]([F:24])=[CH:4][N:3]=1.[CH3:25]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>ClCCl.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[F:24][C:5]1[CH:6]=[C:7]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[C:2]([CH3:25])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of N-(7-(2-chloro-5-fluoropyridin-3-yl)isoquinolin-3-yl)cyclopropanecarboxamide (105.4 mg, 0.3084 mmol), trimethylboroxine (129.0 uL, 0.9228 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (22.3 mg, 0.0315 mmol), and potassium carbonate (112.5 mg, 0.8140 mmol) in 1,4-dioxane (2.0 mL, 26 mmol) was heated at 90° C. for 26 hours. The reaction mixture was then diluted with dichloromethane, washed with water, dried over MgSO4, filtered, and evaporated in vacuo. The crude product was purified via reverse phase HPLC and lyophilized to yield 50.6 mg (51%) of N-(7-(5-fluoro-2-methylpyridin-3-yl)isoquinolin-3-yl)cyclopropanecarboxamide. LCMS (ESI): RT (min)=3.972, M+H=322.0, method=E; 1H NMR (400 MHz, DMSO-d6) δ 10.96 (s, 1H), 9.19 (s, 1H), 8.52 (s, 2H), 8.12 (s, 1H), 7.97 (d, J=8.6 Hz, 1H), 7.86-7.67 (m, 2H), 2.47 (s, 3H), 2.08 (dd, J=12.4, 7.3 Hz, 1H), 0.86 (dd, J=9.3, 6.4 Hz, 4H).

Workup

washwashed with water
dry with materialdried over MgSO4
filtrationfiltered
customevaporated in vacuo
customThe crude product was purified via reverse phase HPLC

Sources & evidence

ORD record: ord-2da1ca01b13d416d9de212ad2714c2a7
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623889B2

Reaction notes

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