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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → [2-(5-Chloro-2-fluoro-phenyl)-quinolin-4-yl]-(3-methoxy-pyridin-4-yl)-amine

HRID 877282
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HRID 877282 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[NH2:28].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]([F:19])=[C:12]([C:4]2[CH:3]=[C:2]([NH:28][C:27]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3[O:21][CH3:20])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 30167383-Methoxy-4-aminopyridineHCID 671727124-Bromo-2-(5-chloro-2-fluoro-phenyl)-quinoline

생성물 1

HCID 67175376[2-(5-Chloro-2-fluoro-phenyl)-quinolin-4-yl]-(3-methoxy-pyridin-4-yl)-amine수율 80.8%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 312751,4-Dioxane용매

실험 절차

250 mg 4-Bromo-2-(5-chloro-2-fluoro-phenyl)-quinoline (cf. Example 5; M 336.59) and 94 mg of 3-methoxy-4-amino pyridine (Tyger Scientific) in 25 ml dioxane were treated under argon with 14 mg Pd2(dba)3 (Aldrich) and 22 mg Xanthphos (ABCR) under basic conditions adjusted with 485 mg Cs2CO3 at 85° C. internal temperature over night. Work-up was conducted by RP HPLC on a Gemini column Axia RP18-100×30 mm/10 μm-110 A. Elution was performed with a 30 min gradient of 1-99% buffer B (=0.3% TFA in CH3CN) in buffer A (=0.3% TFA in water) at 30 ml/min and monitoring at 215 nm. Pooled material after drying yielded 228 mg product of correct mass M+H+ 380 and Rt˜1.74 min in LC-MS system 2.

후처리

  1. washElution
  2. customPooled material after drying

출처 및 근거

ORD 기록
ord-6683359edc2b4153b8adbf0aa95a789e
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987301B2

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