Cesium carbonate → Lhd-221

HRID 1422471노트

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HRID 1422471 반응식
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[N:3]=1.B(O)(O)[C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[S:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl-].CC1C=C(C)C=C(C)C=1[N+]1C=CN(C2C(C)=CC(C)=CC=2C)C=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]>[S:27]1[CH:26]=[C:25]([C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[N:3]=2)[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]1=2

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 27342111,3-Bis(2,4,6-trimethylphenyl)imidazolium chlorideHCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 755299704-(2-((2-Chloro-9-isopropyl-9H-purin-6-yl)amino)ethyl)phenol

생성물 1

HCID 46199207Lhd-221

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
80 °C

실험 절차

A flame-dried schlenk flask was charged with 4-(2-(2-chloro-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol (0.62 mmol), thianaphthene-3-boronic acid (0.94 mmol), pd2(dba)3 (0.062 mmol), Cs2CO3 (1.25 mmol) and 1,3-bis(2,4,6-trimethylphenyl) imidazolium chloride (0.125 mmol). The flask was evacuated and backfilled with N2 and anhydrous 1,4-dioxane (2 mL) was added. The flask was sealed and the reaction mixture was stirred at 80° C. for 24 hours. The reaction mixture was concentrated and purified directly by column chromatography on silica gel, eluting with hexane/EtOAc (20:1 to 1:4) to afford the title compound as a yellowish solid.

후처리

  1. customThe flask was evacuated
  2. additionwas added
  3. customThe flask was sealed
  4. concentrationThe reaction mixture was concentrated
  5. custompurified directly by column chromatography on silica gel
  6. washeluting with hexane/EtOAc (20:1 to 1:4)

출처 및 근거

ORD 기록
ord-0aa1cb5c8d2c48a5b5b79c12fef42d4b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927281B2

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