Water → (2-Methoxy-benzyl)-(5-phenyl-quinolin-2-yl)-amine

HRID 1170073노트

반응식

HRID 1170073 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 67334552(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine

생성물 1

HCID 68433822(2-Methoxy-benzyl)-(5-phenyl-quinolin-2-yl)-amine

시약·촉매·용매 3

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

실험 절차

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.583 mmol) was dissolved in 8 mL 1,2-dimethoxyethane and 4 mL 1M sodium carbonate solution. The reaction mixture was evacuated and backfilled with argon for three times to remove oxygen. Phenylboronic acid (88 mg, 0.699 mmol), palladium(II)acetate (7 mg, 0.029 mmol) and triphenylphosphine (16 mg, 0.058 mmol) were added. The reaction mixture was refluxed overnight. The reaction mixture was poured into 100 mL water and extracted three times with ethyl acetate (100 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). The title compound was obtained as a white solid (191 mg, 96%), MS: m/e=341.3 (M+H+).

후처리

  1. customThe reaction mixture was evacuated
  2. customto remove oxygen
  3. temperatureThe reaction mixture was refluxed overnight
  4. extractionextracted three times with ethyl acetate (100 mL each)
  5. dry with materialThe combined organic extracts were dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

출처 및 근거

ORD 기록
ord-21d65a832b624175ad5713536a122c5a
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825253B2

반응 노트

불러오는 중…