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Triethylamine → Methyl (2s,4r)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-2-carboxylate

HRID 389193
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HRID 389193 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[CH:6]=[C:5]2[O:15][C@H:16]1[CH2:20][N:19](C(OC(C)(C)C)=O)[C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]1.[CH:32]([B-](F)(F)F)=[CH2:33].[K+].CCN(CC)CC>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5]([O:15][C@H:16]3[CH2:20][NH:19][C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]3)=[CH:6][C:7](=[O:14])[NH:8]2)=[CH:3][C:2]=1[CH:32]=[CH2:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 59279885HCID 59279885, 화합물

생성물 1

HCID 59279894Methyl (2s,4r)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-2-carboxylate수율 127.9%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물
촉매
HCID 702Ethanol용매

실험 절차

To a solution of the product from Step 2 (2.26 g, 4.54 mmol) in EtOH (45.4 mL) was added potassium vinyltrifluoroborate (0.913 g, 6.82 mmol), Et3N (0.950 mL, 6.82 mmol), and PdCl2(dppf)-DCM adduct (0.186 g, 0.227 mmol). The reaction mixture was then heated to reflux for 1 hour, cooled to RT; the volatiles were evaporated in vacuo; and the residue partitioned between EtOAc and water. The organic phase was dried over MgSO4, and the solvent was removed in vacuo. The crude material was purified on silica (gradient elution, 0-5% MeOH/DCM) to yield 2.0 g of the title compound. LRMS ESI+ ((M-Boc)+H)+ 345.3.

후처리

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 1 hour
  3. customthe volatiles were evaporated in vacuo
  4. customand the residue partitioned between EtOAc and water
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude material was purified on silica (gradient elution, 0-5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-fbe57c6449e6473b9b6e68ef195e8818
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377874B2

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