Dichloromethane → HCID 86686735, 화합물

HRID 1423321노트

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HRID 1423321 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6](B1OC(C)(C)C(C)(C)O1)=[CH:5]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl.[Cl:32][C:33]1[CH:38]=[C:37]([N:39]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[N:36]2[N:56]=[CH:57][C:58](I)=[C:35]2[N:34]=1>O1CCOCC1.O.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]>[Cl:32][C:33]1[CH:38]=[C:37]([N:39]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:45])[CH3:46])[N:36]2[N:56]=[CH:57][C:58]([C:6]3[CH:7]=[N:8][C:9]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[CH:11][CH:10]=4)=[C:35]2[N:34]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 66584499HCID 66584499, 화합물HCID 772312185-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

생성물 1

HCID 86686735HCID 86686735, 화합물

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

6-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (996.4 mg, 3.65 mmol), K3PO4 (1933.6 mg, 9.12 mmol), and PdCl2(dppf).CH2Cl2 (248 mg, 0.30 mmol) was added to a solution of 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (1684.3 mg, 3.04 mmol) in dioxane (18 mL) and H2O (3 mL). The resulting mixture was stirred at 80° C. under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded 5-chloro-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine: LCMS tR=3.34 Min (5 min run, UV254nm), Mass calculated for, M+573.2, observed LC/MS m/z 574.2 (M+H).

후처리

  1. extractionextracted with ethyl acetate (×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with Na2SO4
  4. customEvaporation and purification by column chromatography

출처 및 근거

ORD 기록
ord-caeb2013bc524637a0eff53fe642d89e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927562B2

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