2,5-Dibromopyridine → HCID 59643333、化合物

HRID 2251524ノート

反応式

HRID 2251524 の反応式
[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

参加物

5

反応物 3

HCID 693532,5-DibromopyridineHCID 81531Diisopropylethylamine2 回HCID 59643115HCID 59643115、化合物

生成物 1

HCID 59643333HCID 59643333、化合物収率 18.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a7b334ceef544331852cb738416c0d21
出典データセット
uspto-grants-2008_01
特許番号
US07319104B2

反応ノート

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