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Sodium Carbonate → N-(3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)phenyl)acrylamide

HRID 1500825
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인쇄 미리보기

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HRID 1500825 반응식
C([NH:5]C1C=C(B(O)O)C=CC=1)(=O)C=C.C([O-])([O-])=O.[Na+].[Na+].[CH3:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[C:28]([C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=3)C=2)[NH:24]N=1>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:5]1[C:28]([C:31]2[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=2)=[CH:27][N:26]=[C:25]2[NH:24][CH:21]=[CH:22][C:30]=12
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 103213313-Acrylamidophenylboronic acidHCID 178460022HCID 178460022, 화합물

생성물 1

HCID 86300986N-(3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)phenyl)acrylamide

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매
HCID 1140
Toluene
용매

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온도
90 °C

실험 절차

A solution of 21 (100 mg, 0.507 mmol) and 2 (84 mg, 0.507 mmol) in toluene and ethanol (4:1 mL) was added Na2CO3 (111.01 mg, 1.014 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (20.7 mg, 0.025 mmol) was added to the reaction. The reaction was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90° C. under sealed condition overnight, allowed to cool to RT, and diluted with chloroform. The organic layer was filtered through Celite and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted in 40% ethyl acetate in hexane as an off-white solid 22. MS-ES+264.8; 1H NMR (400 MHz, DMSO-D6) 22: 9.99 (bs, 1H), 9.40 (bs, 1H), 7.25 (bs, 1H), 7.08 (m, 1H), 7.00 (d, 1H), 6.42 (m, 2H), 6.21 (m, 1H), 5.71 (m, 1H).

후처리

  1. customThe reaction was degassed
  2. custompurged with nitrogen for 10 min
  3. customThe reaction was degassed
  4. custompurged with nitrogen for another 10 min
  5. customunder sealed condition overnight
  6. temperatureto cool to RT
  7. additiondiluted with chloroform
  8. filtrationThe organic layer was filtered through Celite
  9. concentrationconcentrated
  10. customto get the crude, which
  11. customwas purified through flash chromatography
  12. washThe compound was eluted in 40% ethyl acetate in hexane as an off-white solid 22

출처 및 근거

ORD 기록
ord-5d1289de9dd344bf8b0d1ebea005a164
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09206188B2

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