2-Bromopyridine → [2,3'-Bipyridine]-6'-carboxylic acid

HRID 41295ノート

反応式

HRID 41295 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:16]2[CH:17]=[CH:18][C:19]([C:22]([O:24]C)=[O:23])=[N:20][CH:21]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:16]1[CH:21]=[N:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1

参加物

9

反応物 4

HCID 79732-BromopyridineHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 467386632-Methoxycarbonyl-5-pyridineboronic acid, pinacol ester

生成物 1

HCID 57358853[2,3'-Bipyridine]-6'-carboxylic acid収率 23.2%

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

In a 5 ml microwave vial were added 2-bromopyridine (0.093 ml, 0.949 mmol), methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarboxylate (300 mg, 1.139 mmol), bis(triphenylphosphine)palladium(II) chloride (133 mg, 0.190 mmol), sodium carbonate (302 mg, 2.85 mmol), 1,2-dimethoxyethane (1.5 ml), ethanol (1.000 ml) and water (0.500 ml). The reaction mixture was heated for 0.5 hours at 120° C. in the microwave. The mixture was diluted with MeOH and filtered through Celite®. The product was concentrated in vacuo then filtered through a 20 g SCX cartridge (washed with MeOH, eluted with 1M NH3 in MeOH) and evaporated in vacuo. The product was triturated with ether and concentrated under vacuo. The product was diluted in DCM then 1 ml of 1M HCl in ether added and the product was concentrated in vacuo then was dissolved in MeCN/DMSO 1:1 and purified by MDAP. The desired fractions were collected and concentrated under vacuo to give the title compound (44 mg).

後処理

  1. filtrationfiltered through Celite®
  2. concentrationThe product was concentrated in vacuo
  3. filtrationthen filtered through a 20 g SCX cartridge (washed with MeOH, eluted with 1M NH3 in MeOH)
  4. customevaporated in vacuo
  5. customThe product was triturated with ether
  6. concentrationconcentrated under vacuo
  7. additionThe product was diluted in DCM
  8. addition1 ml of 1M HCl in ether added
  9. concentrationthe product was concentrated in vacuo
  10. dissolutionthen was dissolved in MeCN/DMSO 1:1
  11. custompurified by MDAP
  12. customThe desired fractions were collected
  13. concentrationconcentrated under vacuo

出典と根拠

ORDレコード
ord-9ecab71c57fd40988bfeff16b7449608
出典データセット
uspto-grants-2013_09
特許番号
US08530478B2

反応ノート

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