Lithium Chloride → (S)-3-(4-(5-fluoro-2-(pyrimidin-2-yl)pyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

HRID 525411노트

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HRID 525411 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]([CH3:26])([CH3:25])[O:16][C:15]3=[O:27])=[CH:10][CH:9]=2)[C:5]([F:28])=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:34]1[N:39]=[CH:38][CH:37]=[CH:36][N:35]=1)CCC.[Cl-].[Li+]>[Cu]I.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.CN(C=O)C>[F:28][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]([CH3:26])([CH3:25])[O:16][C:15]3=[O:27])=[CH:10][CH:9]=2)=[CH:7][C:2]([C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[N:3][CH:4]=1

참가 물질

7

반응물 3

HCID 433294Lithium ChlorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 89813900(S)-3-(4-(2-bromo-5-fluoropyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

생성물 1

HCID 89813820(S)-3-(4-(5-fluoro-2-(pyrimidin-2-yl)pyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one수율 20%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A microwave vial was charged with (S)-3-(4-(2-bromo-5-fluoropyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.060 g, 0.136 mmol), 2-(tributylstannyl)pyrimidine (commercially available from Frontier Scientific, Inc., Logan Utah) (0.067 mL, 0.204 mmol), lithium chloride (0.012 g, 0.272 mmol), copper (I) iodide (2.59 mg, 0.014 mmol), and DMF (2.0 mL). Tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) was added, the system was purged with argon, and the tube was sealed. The resulting mixture was stirred at 120° C. in a microwave for 1 hour. The reaction mixture was then concentrated to afford an orange oil which was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-10% MeOH-EtOAc) to afford (S)-3-(4-(5-fluoro-2-(pyrimidin-2-yl)pyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.012 g, 0.027 mmol, 20% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.66 (s, 3H), 5.53 (s, 1H), 7.10-7.54 (m, 6H), 7.56-7.89 (m, 5H), 8.10-9.41 (m, 3H). m/z (ESI) 441 (M+H)+.

후처리

  1. customthe system was purged with argon
  2. customthe tube was sealed
  3. concentrationThe reaction mixture was then concentrated
  4. customto afford an orange oil which
  5. customwas purified

출처 및 근거

ORD 기록
ord-00f4f4b4de5a4a84b022863a9faff122
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340549B2

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