Potassium Fluoride → [4-(6-Morpholin-4-ylmethyl-pyridin-3-yl)-naphthalen-1-yl]-oxo-acetic acid

HRID 598715

반응식

HRID 598715 반응식
C([Sn](CCCC)(CCCC)[C:6]1[CH:7]=[CH:8][C:9]([CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:10][CH:11]=1)CCC.C[O:28][C:29](=[O:43])[C:30]([C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](Br)=[CH:34][CH:33]=1)=[O:31].[F-].[K+]>C1CCOCO1.CCOC(C)=O.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>[N:13]1([CH2:12][C:9]2[N:10]=[CH:11][C:6]([C:35]3[C:36]4[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:32]([C:30](=[O:31])[C:29]([OH:43])=[O:28])=[CH:33][CH:34]=3)=[CH:7][CH:8]=2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

참가 물질

7

반응물 3

HCID 522689Potassium FluorideHCID 211363804-(5-Tri-butylstannanyl-pyridin-2-ylmethyl)-morpholineHCID 59379801(4-Bromo-naphthalen-1-yl)-oxo-acetic acid methyl ester

생성물 1

HCID 59379823[4-(6-Morpholin-4-ylmethyl-pyridin-3-yl)-naphthalen-1-yl]-oxo-acetic acid수율 54%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 104501,3-Dioxane용매

반응 조건

온도
150 °C

실험 절차

4-(5-Tri-butylstannanyl-pyridin-2-ylmethyl)-morpholine (0.47 g, 1.59 mmol) and (4-Bromo-naphthalen-1-yl)-oxo-acetic acid methyl ester (18) (0.6 g, 1.3 mmol) and catalytic tetrakis(triphenylphosphine)palladium (0) were dissolved in 2 mL anhydrous 2,4-dioxane under nitrogen atmosphere. The tube was heated under microwave irradiation for 10 minutes at 150° C. After cooling to room temperature the mixture was diluted with EtOAc, and a solution of KF 40% was added. The organic phase was separated and the aqueous layer was evaporated and purified by LC-MS to afford the target product in 54% yield. Calculated mass=376. Observed mass=376.

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. customThe organic phase was separated
  3. customthe aqueous layer was evaporated
  4. custompurified by LC-MS
  5. customto afford the target product in 54% yield

출처 및 근거

ORD 기록
ord-47264462ea5e422fbe2feac9d3fb334f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897599B2

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