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

HRID 1097000노트

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HRID 1097000 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4b4c9fc9a98146f5bc846b0e8d5602d1
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138197B2

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