Dichloromethane → (S)-4-(4-(5-fluoro-2-(methylsulfonyl)phenyl)-6-(3-methylmorpholino)pyrimidin-2-yl)aniline

HRID 1771541노트

반응식

HRID 1771541 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[S:22]([CH3:25])(=[O:24])=[O:23])[N:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)O1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:15]([C:4]2[CH:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]3[CH3:14])[N:7]=[C:2]([C:34]3[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=3)[N:3]=2)[CH:20]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86691149(S)-4-(2-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-4-yl)-3-methylmorpholine2회

생성물 1

HCID 67382304(S)-4-(4-(5-fluoro-2-(methylsulfonyl)phenyl)-6-(3-methylmorpholino)pyrimidin-2-yl)aniline수율 32%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 18180031Water 1,2-dimethoxyethane용매

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온도
120 °C

실험 절차

(S)-4-(2-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 10) (350 mg, 0.91 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (239 mg, 1.09 mmol), Pd(PPh3)2Cl2.DCM (37 mg, 0.05 mmol) and Na2CO3 (145 mg, 1.36 mmol) were dissolved in a mixture of DME:H2O (4:1) and stirred at 120° C. under microwave for 30 mins. The reaction mixture was partitioned between H2O and DCM. The organic layer was recovered, dried over MgSO4, filtered and the solvent removed in vacuo to yield the title compound as a brown solid (128 mg, 0.29 mmol, 32% yield).

후처리

  1. customThe reaction mixture was partitioned between H2O and DCM
  2. customThe organic layer was recovered
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-917551fa02e4402ca313c3ad97f7ab79
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249129B2

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