Sodium Carbonate → (E)-3-{1-[4'-(3-Morpholin-4-yl-propoxy)-biphenyl-3-sulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 2408448

반응식

HRID 2408448 반응식
Br[C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[O:19])=[CH:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:36]2[CH:51]=[CH:50][C:39]([O:40][CH2:41][CH2:42][CH2:43][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:38][CH:37]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[N:44]1([CH2:43][CH2:42][CH2:41][O:40][C:39]2[CH:50]=[CH:51][C:36]([C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([N:11]4[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]5[CH2:27][CH2:26][CH2:25][CH2:24][O:23]5)=[O:19])=[CH:12]4)(=[O:10])=[O:9])[CH:3]=3)=[CH:37][CH:38]=2)[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 46490724-(3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propyl)morpholineHCID 86621698HCID 86621698, 화합물

생성물 1

HCID 86640144(E)-3-{1-[4'-(3-Morpholin-4-yl-propoxy)-biphenyl-3-sulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide수율 78.1%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
100 °C

실험 절차

(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (4.6 g) and 4-{3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-propyl}-morpholine (3.9 g) are dissolved in DME (200 mL). Under an inert gas atmosphere are added are added (Ph3P)3PdCl2 (1.4 g) and 2M Na2CO3-solution (31 mL). The mixture is heated to 100° C. for 2 h. After filtration and extraction, the crude product from the organic phase is purified by silica gel flash chromatography. 4.7 g of the title compound are obtained as brownish oil.

후처리

  1. additionUnder an inert gas atmosphere are added
  2. filtrationAfter filtration and extraction
  3. customthe crude product from the organic phase is purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-0c3a7d2f3ab5490e93a1cd915c6059e3
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815855B2

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