Potassium Phosphate, Tribasic → 2,5-diphenylpyridine

HRID 1897973ノート

反応式

HRID 1897973 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[C:9]1([C:2]2[CH:7]=[CH:6][C:5]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 693532,5-Dibromopyridine

生成物 1

HCID 27628582,5-diphenylpyridine収率 91.8%

試薬・触媒・溶媒 3

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

2,5-dibromopyridine (10 g, 42 mmol), phenylboronic acid (13.4 g, 110 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S-Phos) (0.7 g, 1.6 mmol), and potassium phosphate (22 g, 105 mmol) were mixed in 200 mL of toluene and 20 mL of water. Nitrogen is bubbled directly into the mixture for 30 minutes. Next, Pd2(dba)3 was added (0.38 g, 0.4 mmol) and the mixture was heated to reflux under nitrogen for 2 h. The mixture was cooled and the organic layer was separated. The organic layers are washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue was purified by column chromatography eluting with 10% ethyl acetate/hexanes. 7 g of desired product was obtained after purification. (91.8% yield)

後処理

  1. customNitrogen is bubbled directly into the mixture for 30 minutes
  2. additionNext, Pd2(dba)3 was added (0.38 g, 0.4 mmol)
  3. temperaturethe mixture was heated
  4. temperatureto reflux under nitrogen for 2 h
  5. temperatureThe mixture was cooled
  6. customthe organic layer was separated
  7. washThe organic layers are washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated to a residue
  11. customThe residue was purified by column chromatography
  12. washeluting with 10% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-40e2769d76e74b13b3339a09d724b6f7
出典データセット
uspto-grants-2013_08
特許番号
US08519384B2

反応ノート

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