2-Bromopyridine → HCID 69085397、化合物

HRID 594222ノート

反応式

HRID 594222 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:14]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C1COCC1.O.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>[Cl:8][C:9]1[CH:14]=[C:13]([CH:12]=[C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:10]=1)[C:15]([O:17][CH3:18])=[O:16]

参加物

8

反応物 4

HCID 79732-BromopyridineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 44118784[3-Chloro-5-(methoxycarbonyl)phenyl]boronic acid

生成物 1

HCID 69085397HCID 69085397、化合物

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of commercially available 2-bromopyridine (294 mg; 1.86 mmol), 3-chloro-5-(methoxycarbonyl)phenylboronic acid (400 mg; 1.86 mmol), K2CO3 (515 mg; 3.73 mmol), and PdCl2(PPh3)2 (130 mg; 0.18 mmol) in THF (4 ml) and water (4 ml) was stirred at rt, under nitrogen, for 17 h. Water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=15/1) afforded methyl 3-chloro-5-(pyridin-2-yl)benzoate as a colorless solid. LC-MS (conditions A): tR=0.79 min.; [M+H]+: 247.95 g/mol.

後処理

  1. extractionThe separated aq. layer was further extracted with AcOEt
  2. washThe mixed organic layers were washed with brine
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by FC (DCM/MeOH=15/1)

出典と根拠

ORDレコード
ord-51acc2e8b50849468e22a86db32060f8
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

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