Sodium Carbonate → 3-phenyl-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774966ノート

反応式

HRID 1774966 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[NH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>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]>[C:23]1([C:2]2[C:10]3[C:5](=[CH:6][N:7]=[C:8]([C:11]4[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=4)[CH:9]=3)[NH:4][N:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 178506572HCID 178506572、化合物

生成物 1

HCID 712536843-phenyl-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine収率 60.2%

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 3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine from Example 4 (161 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 phenylboronic acid (74 mg, 0.6 mmol). The mixture was heated in argon under microwave radiation at 135 for 60 min. 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 116 (82 mg, 60%). 1H NMR (400 MHz, DMSO) δ 9.33 (s, 1H), 9.21 (s, 1H), 8.56 (s, 1H), 8.53-8.51 (m, 2H), 8.12-8.10 (m, 2H), 7.57-7.44 (m, 4H). ESI MS m/z=273.7 (M+1

後処理

  1. temperatureThe mixture was heated in argon under microwave radiation at 135 for 60 min
  2. temperatureAfter cooling down
  3. customthe solvent was removed under reduced pressure
  4. 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-3fbda996044a4306acc6c59dc859868e
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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