Water → 4-(6-amino-5-(1-isopropyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-2-methoxybenzoic acid

HRID 1053117ノート

反応式

HRID 1053117 の反応式
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[N:11][N:12]([CH:14]([CH3:16])[CH3:15])[CH:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[C:25]([O:27]C)=[O:26].O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.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>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:21]2[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[C:19]([O:18][CH3:17])[CH:20]=2)=[CH:3][C:4]=1[C:9]1[N:10]=[N:11][N:12]([CH:14]([CH3:16])[CH3:15])[CH:13]=1

参加物

8

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 177502563-Methoxy-4-(methoxycarbonyl)benzeneboronic acidHCID 902731555-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine

生成物 1

HCID 902733904-(6-amino-5-(1-isopropyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-2-methoxybenzoic acid収率 69.4%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To a solution of 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine (300 mg, 1.06 mmol) and (3-methoxy-4-(methoxycarbonyl)phenyl)boronic acid (245 mg, 1.16 mmol) in 1,4-dioxane (10.0 mL)/water (5.0 mL) was added Cs2CO3 (1.0 g, 3.18 mmol) at room temperature. The reaction mixture was degassed with argon for 30 min. Then Pd(PPh3)4 (61 mg, 0.05 mmol) was added and allowed to stir at 120° C. for 30 min in CEM micro wave. The reaction mixture was cooled to RT, diluted with EtOAc (50 mL) and washed with water (50 mL). The aqueous layer was neutralized with 1N HCl, extracted with DCM (2×50 mL), washed with brine solution (20 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure. The crude compound was washed with diethyl ether to afford 260 mg (yield: 69.33%) of the title compound as pale yellow solid.

後処理

  1. customThe reaction mixture was degassed with argon for 30 min
  2. temperatureThe reaction mixture was cooled to RT
  3. washwashed with water (50 mL)
  4. extractionextracted with DCM (2×50 mL)
  5. washwashed with brine solution (20 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customwas evaporated under reduced pressure
  8. washThe crude compound was washed with diethyl ether

出典と根拠

ORDレコード
ord-010899d6bcb84e7594dda2a881929eff
出典データセット
uspto-grants-2016_07
特許番号
US09393248B1

反応ノート

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