Potassium Carbonate → HCID 73335731, compound

HRID 710650

Reaction equation

[Cl:1][C:2]1[C:3]([C:7]([F:10])([F:9])[F:8])=[N:4][NH:5][CH:6]=1.Cl[CH2:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][C:17]2[N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[N:22]=[CH:23][C:16]1=2)=[O:14].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CN(C=O)C>[Cl:1][C:2]1[C:3]([C:7]([F:10])([F:9])[F:8])=[N:4][N:5]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][CH2:18][C:17]3[N:21]([C:24]4[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=4)[N:22]=[CH:23][C:16]2=3)=[O:14])[CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-chloro-3-(trifluoromethyl)pyrazole (0.026 g, 0.15 mmol), 2-chloro-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridine-4-yl]ethanone (0.045 g, 0.15 mmol) and K2CO3 (0.043 g, 0.31 mmol) in THF (0.6 mL) and DMF (0.3 mL) was heated at 60° 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 flash chromatography on SiO2 with a gradient elution of 0-60% EtOAc/hexanes to afford the desired product (0.056 g, 87%). 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 7.70 (s, 1H), 7.45 (m, 2H), 7.16 (dd, J=8.4, 8.4 Hz, 2H), 5.17 (s, 2H), 3.81 (m, 2H), 2.87 (t, J=6.2 Hz, 2H), 2.12 (m, 2H); MS: (ES) m/z calculated for C18H14ClF4N5O [M+H]+ 428.1, found 428.1.

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 flash chromatography on SiO2 with a gradient elution of 0-60% EtOAc/hexanes

Sources & evidence

ORD record: ord-15b2057decb2490ebb93cfc05d246e43
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181241B2

Linked notes

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