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

Cesium fluoride → Tert-butyl 4-[4-[6-amino-5-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate

HRID 908416
노트
인쇄 미리보기

반응식

HRID 908416 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH:13]=2)O1.Br[C:29]1[CH:30]=[C:31]([C:36]2[O:37][C:38]3[C:39]([N:45]=2)=[N:40][CH:41]=[C:42]([F:44])[CH:43]=3)[C:32]([NH2:35])=[N:33][CH:34]=1.[F-].[Cs+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>[NH2:35][C:32]1[N:33]=[CH:34][C:29]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:18][CH2:19]3)[CH:13]=2)=[CH:30][C:31]=1[C:36]1[O:37][C:38]2[C:39]([N:45]=1)=[N:40][CH:41]=[C:42]([F:44])[CH:43]=2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 45480279tert-butyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylateHCID 67388498HCID 67388498, 화합물

생성물 1

HCID 67389039Tert-butyl 4-[4-[6-amino-5-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate수율 87.5%

시약·촉매·용매 2

HCID 6102075
Dichlorobis(triphenylphosphine)palladium
촉매
HCID 887Methanol용매

반응 조건

온도
120 °C

실험 절차

Tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate (222 mg) and 5-bromo-3-(6-fluorooxazolo[4,5-b]pyridin-2-yl)pyridin-2-amine (140 mg), bis(triphenylphosphine) palladium (II) chloride (15.9 mg) and caesium fluoride (172 mg) were weighed out in a microwave vial and sealed. Methanol (2 ml) was added and nitrogen was bubbled in the resulting suspension. The resulting mixture was heated in a 300 W microwave at 120° C. for 20 minutes. The crude product was purified by flash chromatography on silica gel (dried deposit with silica gel) eluting with 0 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford tert-butyl 4-[4-[6-amino-5-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (190 mg). NMR Spectrum: (CDCl3) 1.49 (s, 9H), 1.94-2.03 (m, 2H), 2.16-2.24 (m, 2H), 2.84-3.00 (m, 2H), 3.28 (bs, 2H), 3.29-3.37 (m, 1H), 6.94 (bs, 2H), 7.66 (dd, 1H), 7.68 (s, 1H), 7.79 (s, 1H), 8.35 (d, 1H), 8.45 (d, 1H), 8.48 (dd, 1H); Mass spectrum: M+H+ 480.

후처리

  1. customsealed
  2. customnitrogen was bubbled in the resulting suspension
  3. customThe crude product was purified by flash chromatography on silica gel (dried deposit with silica gel)
  4. washeluting with 0 to 5% methanol in dichloromethane
  5. customThe solvent was evaporated to dryness

출처 및 근거

ORD 기록
ord-efe8c8345f404801824827897ecf7bb8
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017611B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트