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

Cesium carbonate → 7-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264926
노트
인쇄 미리보기

반응식

HRID 2264926 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[C:12]([Cl:15])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH2:16])=[O:5])[CH3:2].[F:17][C:18]1[CH:23]=[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:21]=[CH:20][C:19]=1OS(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].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>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[C:12]([Cl:15])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:19]1[CH:20]=[CH:21][C:22]([Si:24]([CH3:26])([CH3:25])[CH3:27])=[CH:23][C:18]=1[F:17])=[O:5])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59596436Trifluoromethanesulfonic acid 2-fluoro-4-trimethylsilanyl-phenyl esterHCID 59596637ethyl 3-amino-7-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

생성물 1

HCID 595965967-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester
수율 50%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
150 °C

실험 절차

To a solution of 3-amino-7-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (1.0 g, 4.18 mmol) and trifluoromethanesulfonic acid 2-fluoro-4-trimethylsilanyl-phenyl ester (1.45 g, 4.59 mmol) in toluene (18 ml) was added cesium carbonate (1.90 g, 5.85 mmol) before the mixture was degassed. Pd2dba3 (382 mg, 0.418 mmol) and Xantphos (482 mg, 0.835 mmol) were then added and the vessel was flushed with argon. The resultant reaction mixture was heated at 150° C. under microwave irradiation for 31 min, cooled and filtered through Hyflo washing with ethyl acetate. The filtrate was washed with saturated sodium bicarbonate, the organic layer dried (MgSO4) and concentrated in vacuo. Purification of the resultant residue by flash chromatography (Si-PPC, dichloromethane:ethyl acetate gradient 1:0 to 5:1) afforded the title compound as a pale yellow solid (0.84 g, 50%). LCMS (method B): RT=3.75 min, M+H+=406.

후처리

  1. customwas degassed
  2. customthe vessel was flushed with argon
  3. customThe resultant reaction mixture
  4. temperaturecooled
  5. filtrationfiltered through Hyflo
  6. washwashing with ethyl acetate
  7. washThe filtrate was washed with saturated sodium bicarbonate
  8. dry with materialthe organic layer dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customPurification of the resultant residue by flash chromatography (Si-PPC, dichloromethane:ethyl acetate gradient 1:0 to 5:1)

출처 및 근거

ORD 기록
ord-de0a64fb106c43e184ba32d9fb20687b
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07855216B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트