Sodium Carbonate → 5-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carboxamide

HRID 733125노트

반응식

HRID 733125 반응식
C([C:3]1[C:4]([C:16]([NH2:18])=[O:17])=[N:5][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11](Br)[CH:10]=2)[C:7]=1[CH3:8])C.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC.C1(C)C=CC=CC=1.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>[CH3:8][C:7]1[N:6]([C:9]2[CH:10]=[C:11]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][C:20]([F:19])([F:32])[F:31])[CH:12]=[CH:13][CH:14]=2)[N:5]=[C:4]([C:16]([NH2:18])=[O:17])[CH:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 69062233ethyl 1-(3-bromophenyl)-5-methyl-1H-pyrazole-3-carboxamide

생성물 1

HCID 99508045-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carboxamide수율 93.4%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 22495535HCID 22495535, 화합물용매

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온도
90 °C

실험 절차

To a solution of ethyl 1-(3-bromophenyl)-5-methyl-1H-pyrazole-3-carboxamide (0.237 g, 0.8 mmol) and 2-trifluoromethoxyphenyl boronic acid (0.262 g, 1.2 mmol) in n-propanol/toluene (1.27 ml:0.42 ml) mixture were added tetrakis(triphenylphosphine)palladium (0.019 g, 0.01 mmol) and 2M sodium carbonate (0.84 ml). The reaction mixture was heated at 90° C. for 16 hours, and then cooled and partitioned between ethyl acetate and water. The organic phase was washed with saturated sodium bicarbonate and brine, then dried over sodium sulfate and concentrated. The crude product was purified by silica-gel column chromatography (3.5:1.5 hexanes/acetone) to give the product (0.270 g, 88%) as a solid.

후처리

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by silica-gel column chromatography (3.5:1.5 hexanes/acetone)

출처 및 근거

ORD 기록
ord-81c0a498528944c4a627c9d2b4bdaf35
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589116B2

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