Tetrahydrofuran → Methyl 1-methyl-3-phenyl-1H-indazole-6-carboxylate

HRID 1097000ノート

反応式

HRID 1097000 の反応式
C1COCC1.I[C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=2)[N:9]([CH3:20])[N:8]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C.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].O>[CH3:20][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2)[C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:8]1

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 57931017Methyl 3-iodo-1-methyl-1H-indazole-6-carboxylate

生成物 1

HCID 57931013Methyl 1-methyl-3-phenyl-1H-indazole-6-carboxylate

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

In a 100-mL egg plant-type flask, PdCl2(dppf) (178 mg, 0.22 mmol) was added to a THF (20 mL)-water (2 mL) mixed solution of methyl 3-iodo-1-methyl-1H-indazole-6-carboxylate (690 mg, 22 mmol), phenylboric acid (399 mg, 3.27 mmol) and K2CO3 (1.35 g, 9.81 mmol), and stirred overnight at 80° C. in an argon atmosphere. This was diluted with ethyl acetate, washed with water and saturated saline water, dried with sodium sulfate, filtered and concentrated. The resulting crude product was purified through silica gel column chromatography to obtain the title compound.

後処理

  1. washwashed with water and saturated saline water
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude product was purified through silica gel column chromatography

出典と根拠

ORDレコード
ord-4b4c9fc9a98146f5bc846b0e8d5602d1
出典データセット
uspto-grants-2012_03
特許番号
US08138197B2

反応ノート

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