Potassium Carbonate → Trifluoroacetic acid

HRID 60899

反応式

HRID 60899 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH3:17])[C@H:12]1[CH2:18][NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1)=[O:10].CC1(C)C(C)(C)OB([C:38]2[CH:39]=[N:40][N:41]([C:43]([O:45]C(C)(C)C)=[O:44])[CH:42]=2)O1.C([O-])([O-])=O.[K+].[K+]>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.O1CCOCC1.O>[CH3:17][C@@H:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:9]([C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[C:38]2[CH:39]=[N:40][NH:41][CH:42]=2)=[O:10])[C@@H:12]1[CH2:18][NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1.[C:43]([OH:45])([C:26]([F:29])([F:28])[F:27])=[O:44]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 89739735(2-Bromo-5-methylphenyl)((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone

生成物 2

HCID 6422Trifluoroacetic acidHCID 117727670((2S,3R)-3-Methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(5-methyl-2-(1H-pyrazol-4-yl)phenyl)methanone

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
100 °C

実験手順

A mixture of (2-bromo-5-methylphenyl)((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone (0.045 g, 0.097 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (0.034 g, 0.116 mmol), Pd(PPh3)4 (0.017 g, 0.015 mmol), K2CO3 (0.4 g, 0.291 mmol) and dioxane/H2O (4:1, 3 mL) was degassed for 5 min and heated overnight at 100° C. The completion of the reaction was monitored by anal. HPLC. The mixture was cooled and extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3 and dried over Na2SO4. The solvent was removed in vacuo to obtain the crude, which was purified by preparative-HPLC to obtain the title compound as TFA salt. ESI-MS (m/z): 458 [M+1]+.

後処理

  1. customwas degassed for 5 min
  2. temperatureThe mixture was cooled
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo
  7. customto obtain the crude, which
  8. customwas purified by preparative-HPLC

出典と根拠

ORDレコード
ord-537d6262b3974b449257b36e565883b1
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

関連ノート

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