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Sodium Carbonate → 1-(2-(7-Methoxyquinolin-4-yloxy)propyl)-5-(thiophen-2-yl)pyridin-2(1H)-one

HRID 1878700
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HRID 1878700 반응식
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:24])[N:6]([CH2:8][CH:9]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[CH3:10])[CH:7]=1.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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]>[CH3:23][O:22][C:18]1[CH:17]=[C:16]2[C:21]([C:12]([O:11][CH:9]([CH3:10])[CH2:8][N:6]3[CH:7]=[C:2]([C:26]4[S:25][CH:29]=[CH:28][CH:27]=4)[CH:3]=[CH:4][C:5]3=[O:24])=[CH:13][CH:14]=[N:15]2)=[CH:20][CH:19]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 598430605-Bromo-1-(2-(7-methoxyquinolin-4-yloxy)propyl)pyridin-2(1H)-one

생성물 1

HCID 250186391-(2-(7-Methoxyquinolin-4-yloxy)propyl)-5-(thiophen-2-yl)pyridin-2(1H)-one

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

A suspension of 5-bromo-1-(2-(7-methoxyquinolin-4-yloxy)propyl)pyridin-2(1H)-one (20 mg, 51 μmol), thiophen-2-ylboronic acid (13 mg, 103 μmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (2 mg, 3 μmol), and Na2CO3 (77 μl, 154 μmol) in DME (0.5 mL) was heated to 80° C. for 2 h. The mixture was purified on RP-HPLC and the product was netralized with CH2Cl2/NaOH (1 M). The product was lyophilized from 1:1 acetonitrile/water (1 mL) to give a white fluffy powder. MS (ESI pos. ion) m/z (MH+): 393. Calc'd exact mass for C22H20N2O3S: 392. 1H NMR (400 MHz, Chloroform-d) δ ppm 1.55 (d, J=6.02 Hz, 3H) 3.49 (d, J=3.01 Hz, 1H) 3.91 (s, 3H) 4.03 (dd, J=13.55, 8.03 Hz, 1H) 4.58 (dd, J=13.55, 3.01 Hz, 1H) 5.10-5.22 (m, 1H) 6.58 (d, J=9.54 Hz, 1H) 6.66 (d, J=5.02 Hz, 1H) 6.88 (d, J=3.01 Hz, 1H) 6.96-7.01 (m, 1H) 7.05 (dd, J=9.03, 2.51 Hz, 1H) 7.19 (d, J=5.02 Hz, 1H) 7.30 (d, J=2.01 Hz, 1H) 7.52 (dd, J=9.54, 2.51 Hz, 1H) 7.63 (d, J=2.51 Hz, 1H) 8.05 (d, J=9.03 Hz, 1H) 8.59 (d, J=5.52 Hz, 1H). 13C NMR (101 MHz, Chloroform-d) δ ppm 17.37, 53.44, 55.03, 55.49, 71.85, 100.05, 107.33, 114.41, 116.10, 118.50, 120.89, 122.78, 124.20, 127.97, 135.11, 138.95, 139.26, 151.43, 151.71, 160.01, 160.98, 161.84.

후처리

  1. customThe mixture was purified on RP-HPLC
  2. customto give a white fluffy powder

출처 및 근거

ORD 기록
ord-f20cba035ae04917acfdd94c7014adfe
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08314087B2

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