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5-bromo-7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole → (6-chloro-pyrimidin-4-yl)-[7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-methanone

HRID 469306
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인쇄 미리보기

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HRID 469306 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:6]=[CH:5]2.C([Li])CCC.CON(C)[C:28]([C:30]1[CH:35]=[C:34]([Cl:36])[N:33]=[CH:32][N:31]=1)=[O:29]>C1COCC1>[Cl:36][C:34]1[N:33]=[CH:32][N:31]=[C:30]([C:28]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([CH3:11])[CH:10]=2)[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:6]=[CH:5]3)=[O:29])[CH:35]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 581812085-bromo-7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazoleHCID 581812166-Chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amideHCID 178418339Butyllithium

생성물 1

HCID 58181210(6-chloro-pyrimidin-4-yl)-[7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
2회

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온도
-75 °C

실험 절차

Under an argon atmosphere 0.34 g (1.00 mmol) 5-bromo-7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole in 10 mL THF were cooled to −75° C., mixed with 0.70 mL (1.1 mmol) of a 1.6 molar n-butyllithium solution and stirred for 1 h at −75° C. Then 0.25 g (1.1 mmol) 6-chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amide, dissolved in a little THF, were added dropwise. The cooling bath was removed and the mixture was heated to 0° C. and stirred for a further hour in the ice bath. The mixture was stirred with saturated sodium hydrogen carbonate solution, extracted with EtOAc, the organic phase was dried and evaporated down. The residue was purified by flash chromatography.

후처리

  1. additionwere added dropwise
  2. customThe cooling bath was removed
  3. temperaturethe mixture was heated to 0° C.
  4. stirringstirred for a further hour in the ice bath
  5. stirringThe mixture was stirred with saturated sodium hydrogen carbonate solution
  6. extractionextracted with EtOAc
  7. customthe organic phase was dried
  8. customevaporated down
  9. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-79699a7416d048da97bd66966e2eff2c
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08629137B2

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