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

HRID 1880393
ノート
印刷プレビュー

反応式

HRID 1880393 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 22663384HCID 22663384、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
触媒
HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-120ef0eeb703433da63bed576701cda6
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318762B2

反応ノート

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