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

HRID 524946

반응식

HRID 524946 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 312751,4-Dioxane용매

실험 절차

[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.

후처리

  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

출처 및 근거

ORD 기록
ord-0eacb3f7f5ae4292b652bcf623f15182
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340546B2

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