Morpholine → 4-[(5-Bromopyridin-3-yl)acetyl]morpholine

HRID 712762노트

반응식

HRID 712762 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[O:11])[CH:5]=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 8083MorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

생성물 1

HCID 189859944-[(5-Bromopyridin-3-yl)acetyl]morpholine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To the solution of 5-bromo-3-pyridineacetic acid (500 mg, 2.314 mmol) in DMF (3 mL) is added TBTU (1.11 g, 3.472 mmol). Morpholine (0.61 mL, 6.94 mmol) is added dropwise and the mixture is stirred at room temperature for 18 h. The mixture is diluted with EtOAc (50 mL), washed with water (3×5 mL), and brine, dried over sodium sulfate, filtered, and concentrated. The resulting crude product is purified by normal phase chromatography using 0-4.5% MeOH in DCM as the gradient to afford 2-(5-bromo-pyridin-3-yl)-1-morpholin-4-yl-ethanone.

후처리

  1. washwashed with water (3×5 mL), and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude product is purified by normal phase chromatography

출처 및 근거

ORD 기록
ord-9716dbba41f443b7ba5e7771cc66c647
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181272B2

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