Acetonitrile → (S)-tert-butyl (1-(7-fluoro-2-(2-(methylthio)phenyl)quinolin-3-yl)ethyl)carbamate

HRID 75361

반응식

HRID 75361 반응식
Cl[C:2]1[C:11]([C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:22])=[CH:7][CH:8]=2)[N:3]=1.[CH3:23][S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CC#N>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:22][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[C:11]([C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[C:2]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[S:24][CH3:23])=[N:3]2)=[CH:8][CH:7]=1

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 86698502(S)-tert-butyl (1-(2-chloro-7-fluoroquinolin-3-yl)ethyl)carbamate

생성물 1

HCID 86698501(S)-tert-butyl (1-(7-fluoro-2-(2-(methylthio)phenyl)quinolin-3-yl)ethyl)carbamate수율 94.8%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

A mixture of (S)-tert-butyl (1-(2-chloro-7-fluoroquinolin-3-yl)ethyl)carbamate (382 mg, 1.2 mmol), 2-(methylthio)phenylboronic acid (257 mg, 1.3 eq), Na2CO3 (623 mg, 5.0 eq), Pd(PPh3)4 (93 mg, 5%), MeCN (9 mL) and water (3 mL) was heated to 85° C. under N2 overnight. After cooling to rt, the reaction was partitioned between EtOAc (10 mL) and water (5 mL). The organic layer was separated, washed, dried and concentrated. The residue was purified by column chromatography on silica gel to give a white solid (S)-tert-butyl (1-(7-fluoro-2-(2-(methylthio)phenyl)quinolin-3-yl)ethyl)carbamate (460 mg, 94.8%). Mass Spectrum (ESI) m/e=413 (M+1).

후처리

  1. temperatureAfter cooling to rt
  2. customthe reaction was partitioned between EtOAc (10 mL) and water (5 mL)
  3. customThe organic layer was separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-f4e0eee6cf5b42bba0ce16d404add6d2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835432B2

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