Potassium Carbonate → HCID 73335822, compound

HRID 710653Notes

Reaction equation

[F:1][C:2]([F:9])([F:8])[C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.Cl[CH2:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][C:16]2[N:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:21]=[CH:22][C:15]1=2)=[O:13].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CN(C=O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]([N:20]2[C:16]3[CH2:17][CH2:18][CH2:19][N:14]([C:12](=[O:13])[CH2:11][N:5]4[CH:4]=[C:3]([C:2]([F:9])([F:8])[F:1])[CH:7]=[N:6]4)[C:15]=3[CH:22]=[N:21]2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 4-(trifluoromethyl)-1H-pyrazole (0.030 g, 0.22 mmol), 2-chloro-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridine-4-yl]ethanone (0.025 g, 0.085 mmol) and K2CO3 (0.060 g, 0.43 mmol) in THF (0.8 mL) and DMF (0.4 mL) was heated at 65° C. for 1 hr. It was then cooled to rt. The mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo and purified by reverse phase HPLC to afford the desired product (0.038 g, 100%). 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 7.89 (s, 1H), 7.77 (s, 1H), 7.44 (dd, J=8.8, 4.6 Hz, 2H), 7.16 (dd, J=8.8, 8.4 Hz, 2H), 5.20 (s, 2H), 3.83 (m, 2H), 2.85 (t, J=6.2 Hz, 2H), 2.10 (m, 2H); MS: (ES) m/z calculated for C18H15F4N5O [M+H]+ 394.1, found 394.1.

Workup

temperatureIt was then cooled to rt
customThe mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL)
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-a1db2aefe58b47c6a2550185b0f8b058
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181241B2

Reaction notes

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