Potassium Carbonate → HCID 73335731、化合物

HRID 710650

反応式

HRID 710650 の反応式
[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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 867116682-chloro-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridine-4-yl]ethanoneHCID 178506300HCID 178506300、化合物

生成物 1

HCID 73335731HCID 73335731、化合物収率 87.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  1. temperatureIt was then cooled to rt
  2. customThe mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography on SiO2 with a gradient elution of 0-60% EtOAc/hexanes

出典と根拠

ORDレコード
ord-15b2057decb2490ebb93cfc05d246e43
出典データセット
uspto-grants-2015_11
特許番号
US09181241B2

関連ノート

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