2,5-Dibromopyridine → HCID 59643333, 화합물

HRID 2251524노트

반응식

HRID 2251524 반응식
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][N:32]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[Br:37][C:34]1[CH:35]=[CH:36][C:31]([N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=2)[CH2:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:12]=2)=[N:32][CH:33]=1

참가 물질

5

반응물 3

HCID 693532,5-DibromopyridineHCID 81531Diisopropylethylamine2회HCID 59643115HCID 59643115, 화합물

생성물 1

HCID 59643333HCID 59643333, 화합물수율 18.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (3 g; 7.3 mmol) in 7 ml of dioxane was treated under nitrogen with 2,5-dibromopyridine (1.9 g; 8.1 mmol) and DIEA (1.4 ml; 8.1 mmol) and heated in a pressure tube for 2 days at 210C. Upon cooling, additional DIEA (1.4 ml) was added and heated 2 more days. Upon cooling, the reaction mixture was partitioned between ethyl acetate and 0.5N HCl. The organic phase was washed with 0.5N HCl and saturated brine, dried over sodium sulfate and concentrated. Purification by silica gel chromatography using an ethyl acetate-hexane gradient (5–60%) afforded the title compound (0.75 g; 18% yield).

후처리

  1. temperatureUpon cooling
  2. temperatureheated 2 more days
  3. temperatureUpon cooling
  4. customthe reaction mixture was partitioned between ethyl acetate and 0.5N HCl
  5. washThe organic phase was washed with 0.5N HCl and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-a7b334ceef544331852cb738416c0d21
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319104B2

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