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Methanol → Methyl 1-triflyl-3-methyl-indazole-6-carboxylate

HRID 1880393
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HRID 1880393 반응식
FC(F)(F)S(O[C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH3:23])=[N:12][N:13]2[S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])=[CH:9][CH:8]=1)(=O)=O.[CH2:26](N(CC)CC)C.[CH3:33][OH:34].[OH2:35]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:23][C:11]1[C:10]2[C:14](=[CH:15][C:7]([C:33]([O:35][CH3:26])=[O:34])=[CH:8][CH:9]=2)[N:13]([S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[N:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 22663384HCID 22663384, 화합물

생성물 1

HCID 22663352Methyl 1-triflyl-3-methyl-indazole-6-carboxylate수율 69%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
촉매
HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-methyl-1-[(trifluoromethyl)sulfonyl]-1H-indazol-6-yl trifluoromethanesulfonate (0.61 g, 1.5 mmol) in DMF (6 mL) was flushed with CO for 5 minutes. The solution was treated with palladium acetate (68 mg, 0.30 mmol), 1,1′-bis(diphenylphosphino)ferrocene (167 mg, 0.30 mmol), triethylamine (0.33 g, 0.45 mL, 3.2 mmol) and methanol (4 mL). The mixture was stirred at room temperature under CO (1 atm). The solution was poured into water and extracted with EtOAc (3×). The combined organic extracts were concentrated and purified by Biotage (40S column, 8% EtOAc/heptane) to provide methyl 3-methyl-1-[(trifluoromethyl)sulfonyl]-1H-indazole-6-carboxylate (330 mg, 69%).

후처리

  1. extractionextracted with EtOAc (3×)
  2. concentrationThe combined organic extracts were concentrated
  3. custompurified by Biotage (40S column, 8% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-120ef0eeb703433da63bed576701cda6
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318762B2

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