Phenyl-3-pyridinylmethanone → HCID 86716141, 화합물

HRID 627565

반응식

HRID 627565 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:5]2[C:22]([F:25])([F:24])[F:23].[Li]CCCC.[C:31]1([C:37]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[C:31]1([C:37]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([C:12]([F:14])([F:13])[F:15])[C:6]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:5]3[C:22]([F:23])([F:24])[F:25])([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)[OH:38])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

참가 물질

5

반응물 3

HCID 21540Phenyl-3-pyridinylmethanoneHCID 86716066HCID 86716066, 화합물2회HCID 178418339Butyllithium

생성물 1

HCID 86716141HCID 86716141, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A ˜−70° C. solution of 6-bromo-3-phenyl-2,4-bis(trifluoromethyl)quinoline (66.8 mg, 0.159 mmol, Intermediate 8, step c) in THF (0.9 mL) was treated dropwise with n-BuLi (0.12 mL, 1.59 M, 0.191 mmol) via syringe under argon over 1 min. After stirring for less than 1 min, the dark homogeneous solution was treated with a solution of phenyl(pyridin-3-yl)methanone (32.0 mg, 0.175 mmol, Aldrich) in THF (0.6 mL) over 2 min, and the resulting dark amber solution was stirred at ˜−70° C. while the cold bath was allowed to expire over 4 hours. The amber solution was then partitioned with 5 M NH4Cl (2 mL) and EtOAc (5 mL), and the organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by C18 HPLC (20% to 100% CH3CN, with 0.1% TFA throughout) to provide, after lyophilization, the title compound as a white solid. 1H NMR (400 MHz, MeOH-d4) δ 8.87 (s, 1H), 8.78 (d, J=5.38 Hz, 1H), 8.47 (d, J=8.07 Hz, 1H), 8.27-8.39 (m, 2H), 7.92-8.05 (m, 2H), 7.26-7.54 (m, 10H); MS m/e 568.0 [M+H]+.

후처리

  1. stirringthe resulting dark amber solution was stirred at ˜−70° C. while the cold bath
  2. customThe amber solution was then partitioned with 5 M NH4Cl (2 mL) and EtOAc (5 mL)
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by C18 HPLC (20% to 100% CH3CN, with 0.1% TFA throughout)
  7. customto provide

출처 및 근거

ORD 기록
ord-427c811a7af94e3f8d341e25627090f9
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309222B2

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