홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Toluene → Ethyl 2-(4-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylamino)nicotinate

HRID 1676410
노트
인쇄 미리보기

반응식

HRID 1676410 반응식
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])([O-])=O.[Cs+].[Cs+].[NH2:19][C:20]1[CH:48]=[CH:47][C:23]([O:24][C:25]2[CH:30]=[CH:29][N:28]=[C:27]3[CH:31]=[C:32]([CH:34]4[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]4)[S:33][C:26]=23)=[C:22]([F:49])[CH:21]=1.C1(C)C=CC=CC=1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCO>[C:43]([O:42][C:40]([N:37]1[CH2:38][CH2:39][CH:34]([C:32]2[S:33][C:26]3[C:27](=[N:28][CH:29]=[CH:30][C:25]=3[O:24][C:23]3[CH:47]=[CH:48][C:20]([NH:19][C:2]4[N:12]=[CH:11][CH:10]=[CH:9][C:3]=4[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:21][C:22]=3[F:49])[CH:31]=2)[CH2:35][CH2:36]1)=[O:41])([CH3:46])([CH3:44])[CH3:45]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 2796614Ethyl chloronicotinateHCID 67346565Tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)piperidine-1-carboxylate

생성물 1

HCID 67345485Ethyl 2-(4-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylamino)nicotinate수율 65.5%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

A microwave vial was charged with ethyl 2-chloronicotinate (0.209 g, 1.13 mmol), Cs2CO3 (0.331 g, 1.01 mmol), tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)piperidine-1-carboxylate (Example 154, Step A, 0.200 g, 0.451 mmol), Palladium acetate (0.0101 g, 0.0451 mmol), PdCl2(dppf)-dcm (0.0185 g, 0.0225 mmol), toluene (2 mL) and EtOH (1 mL). The mixture was heated to 110° C. for 3 hours. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc. The organics were isolated and dried (MgSO4). After filtration and concentration, the crude product was purified by preparative TLC (2.0 mm thickness, eluting with EtOAc. The product (175 mg, 59%) was isolated as a yellow solid. LRMS (esi+)593 m/z (M+1) detected.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. customThe organics were isolated
  4. dry with materialdried (MgSO4)
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by preparative TLC (2.0 mm thickness
  7. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-701cdff1304f4e59af3b69c89e3a7cc4
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08003662B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트