Sodium Carbonate → HCID 86676682、化合物

HRID 1774956ノート

反応式

HRID 1774956 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][NH:8][C:5]2=[CH:6][N:7]=1.C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OB([C:25]2[CH:26]=[N:27][NH:28][CH:29]=2)O1>COCCOC.CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:27]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]3[CH:10]=[N:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH:29]=[N:28]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 457897785-Bromo-1H-pyrazolo[3,4-c]pyridine

生成物 1

HCID 86676682HCID 86676682、化合物収率 43.2%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 20074477Dimethoxyethane ethanol溶媒

実験手順

To a solution of 5-bromo-1H-pyrazolo[3,4-c]pyridine (100 mg, 0.5 mmol) in DME:EtOH (5:1, 5 mL) was added Pd(dppf)Cl2 (20 mg), saturated solution of Na2CO3 (1 mL) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (116 mg, 0.6 mmol). Under argon, the mixture was stirred under microwave irradiation for 60 min at 150. After cooling down, the solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1) to afford 5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine (40 mg, 43%). 1H NMR (500 MHz, MeOD) δ 9.17 (s, 1H), 8.98 (s, 1H), 8.17 (m, 3H), 8.05 (d, J=1.5, 1H). ESI MS m/z=186.1 (M+1).

後処理

  1. temperatureAfter cooling down
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1)

出典と根拠

ORDレコード
ord-319b0a66eaf34230a59f91521b0792d6
出典データセット
uspto-grants-2016_02
特許番号
US09260425B2

反応ノート

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