Triphenylphosphine → 3'-Methyl-[4,4'-bipyridin]-3-amine

HRID 524946

反応式

HRID 524946 の反応式
C(OC([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1B(O)O)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:38]1[CH:43]=[CH:42][N:41]=[CH:40][C:39]=1[CH3:44].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Pd]>[CH3:44][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][C:38]=1[C:14]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:8]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 4283514-Bromo-3-methylpyridineHCID 15366412(3-((tert-Butoxycarbonyl)amino)pyridin-4-yl)boronic acid

生成物 1

HCID 831677843'-Methyl-[4,4'-bipyridin]-3-amine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

[3-(tert-butoxycarbonylamino)-4-pyridyl]boronic acid (100 mg, 0.4201 mmol), palladium; triphenylphosphane (48.55 mg, 0.04201 mmol), 4-bromo-3-methyl-pyridine (113.9 mg, 0.5461 mmol), K3PO4 (630.0 μL of 2 M, 1.260 mmol), in dioxane (4.000 mL) was heated at 130° C. for 30 min in a MW. The reaction mixture was partitioned between water and DCM. Combined organic extract was dried and concentrated in vacuo. The residue was dissolved in DCM (10 mL) and TFA (2 mL) was added. After 1 h, the reaction mixture was concentrated in vacuo. The residue was loaded on a SCX column, washed with MeOH. The product was eluted with a 2M NH3 in MeOH., filtrate was concentrated in vacuo yielding 3′-methyl-[4,4′-bipyridin]-3-amine that was used in next reaction w/o further purification (90 mg). MS (ES+) 172.1.

後処理

  1. customThe reaction mixture was partitioned between water and DCM
  2. extractionCombined organic extract
  3. customwas dried
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in DCM (10 mL)
  6. additionTFA (2 mL) was added
  7. concentrationthe reaction mixture was concentrated in vacuo
  8. washwashed with MeOH
  9. washThe product was eluted with a 2M NH3 in MeOH
  10. concentration, filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-0eacb3f7f5ae4292b652bcf623f15182
出典データセット
uspto-grants-2016_05
特許番号
US09340546B2

関連ノート

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