Water → 1,1-Dimethylethyl 4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-1-piperazinecarboxylate

HRID 2246632노트

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HRID 2246632 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:24]([NH:26][C:27](=[O:45])[C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[C:31]([CH3:43])=[C:30]([F:44])[CH:29]=1)[CH3:25].C(=O)([O-])O.[Na+].O>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH2:24]([NH:26][C:27]([C:28]1[CH:29]=[C:30]([F:44])[C:31]([CH3:43])=[C:32]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([N:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]4)=[N:7][NH:8]3)=[CH:4][CH:3]=2)[CH:33]=1)=[O:45])[CH3:25]

참가 물질

8

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 57416242N-ethyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2회HCID 58899616HCID 58899616, 화합물2회

생성물 1

HCID 588996101,1-Dimethylethyl 4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-1-piperazinecarboxylate수율 45.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 3776Isopropanol용매HCID 6344Dichloromethane용매

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온도
150 °C

실험 절차

A mixture of 1,1-dimethylethyl 4-(6-bromo-1H-indazol-3-yl)-1-piperazinecarboxylate (Intermediate 6, 28 mg), N-ethyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5, 27 mg), tetrakis(triphenylphosphine)palladium (2 mg) and aqueous sodium hydrogen carbonate (0.125 ml) in isopropanol (0.5 ml) was heated at 150° C. in a microwave oven for 15 min. Water and DCM were added and the organic phase was separated using a hydrophobic filter tube. The solvent was evaporated and the residue was purified by reverse phase preparative HPLC to give the title compound (16 mg).

후처리

  1. customthe organic phase was separated
  2. customThe solvent was evaporated
  3. customthe residue was purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-96af7a04149c474fa92170fcf0d5ff86
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687532B2

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