Triphenylphosphine → (6-Chloro-4-pyridin-3-yl-quinolin-2-yl)-(2-methoxy-benzyl)-amine

HRID 1949022노트

반응식

HRID 1949022 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH:3]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[CH:3]=[C:2]2[C:25]1[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=1

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 27343783-Pyridinylboronic acidHCID 68574963(4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine

생성물 1

HCID 68574847(6-Chloro-4-pyridin-3-yl-quinolin-2-yl)-(2-methoxy-benzyl)-amine

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

실험 절차

(4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine (530 mg, 1.4 mmol) and pyridine-3-boronic acid (224 mg, 1.8 mmol) were dissolved in 16 mL dimethoxyethane and 8 mL 2N sodium carbonate solution. The reaction mixture was evacuated and backfilled with argon for three times. Triphenylphosphine (37 mg, 0.141 mmol) and palladium acetate (16 mg, 0.071 mmol) were added and the mixture was refluxed overnight. The mixture was extracted three times with ethyl acetate (200 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->30:70 gradient). (6-Chloro-4-pyridin-3-yl-quinolin-2-yl)-(2-methoxy-benzyl)-amine was obtained as a white foam (500 mg, 94%), MS: m/e=376.4 (M+H+).

후처리

  1. customThe reaction mixture was evacuated
  2. temperaturethe mixture was refluxed overnight
  3. extractionThe mixture was extracted three times with ethyl acetate (200 mL each)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->30:70 gradient)

출처 및 근거

ORD 기록
ord-563f7d21d34f42e09dd7846450427068
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399674B2

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