Sodium Bicarbonate → 3-(1-benzyl-1H-pyrazol-4-yl)-2-chloropyridine

HRID 883025ノート

反応式

HRID 883025 の反応式
[CH2:1]([N:8]1[CH:12]=[C:11](I)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:14][C:15]1[C:20](B(O)O)=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH:12]=[C:11]([C:20]2[C:15]([Cl:14])=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 2762704(2-Chloropyridin-3-yl)boronic acidHCID 37945791-Benzyl-4-iodo-1H-pyrazole

生成物 1

HCID 866237863-(1-benzyl-1H-pyrazol-4-yl)-2-chloropyridine

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
85 °C

実験手順

1-Benzyl-4-iodo-1H-pyrazole (1.35 g, 4.77 mmol), 2-chloropyridin-3-ylboronic acid (1.50 g, 9.53 mmol), sodium bicarbonate (1.20 g, 14.3 mmol) and Pd(PPh3)4 (276 mg, 0.239 mmol) were combined in an argon-purged sealed tube. Dimethoxyethane (8 mL) and water (5 mL) were added and the mixture was heated to 85° C. for 16 hours. The reaction was cooled to rt, diluted with water and extracted into EtOAc. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. This residue was purified by silica gel chromatography (50-75% EtOAc/hexanes) to yield 3-(1-benzyl-1H-pyrazol-4-yl)-2-chloropyridine as a light yellow oil after concentration. MS m/z=270 [M+1]+. Calc'd for C15H12FN3: 269.74.

後処理

  1. custompurged
  2. customsealed tube
  3. additionDimethoxyethane (8 mL) and water (5 mL) were added
  4. temperatureThe reaction was cooled to rt
  5. additiondiluted with water
  6. extractionextracted into EtOAc
  7. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThis residue was purified by silica gel chromatography (50-75% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-2a1f22fc0bae4191895be2d94dc9f531
出典データセット
uspto-grants-2012_08
特許番号
US08236823B2

反応ノート

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