Cesium carbonate → HCID 66690540、化合物

HRID 592289ノート

反応式

HRID 592289 の反応式
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16](Cl)[N:17]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([C:23]2[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=2)[N:17]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 214303362-Chloro-6-[(phenylmethyl)amino]-4-pyridinecarboxylic acid

生成物 1

HCID 66690540HCID 66690540、化合物収率 57.7%

試薬・触媒・溶媒 3

HCID 53485975CID 53485975触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2-(benzylamino)-6-chloroisonicotinic acid (0.9 g, 3.43 mmol) in THF (8.57 mL) and water (8.57 mL) were added (4-methylphenyl)boronic acid (0.70 g, 5.14 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.14 g, 0.17 mmol) and cesium carbonate (3.35 g, 10.3 mmol). The mixture was purged with nitrogen and was heated to 120° C. in the microwave reactor for 7 min. The mixture was filtered with Celite and saturated aqueous sodium bicarbonate was added. The mixture was extracted with ethyl acetate (3×). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→80% dichloromethane/methanol) gave the title compound (0.63 g): LC-MS [M+1]=318.9.

後処理

  1. customThe mixture was purged with nitrogen
  2. filtrationThe mixture was filtered with Celite and saturated aqueous sodium bicarbonate
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate (3×)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (100% dichloromethane→80% dichloromethane/methanol)

出典と根拠

ORDレコード
ord-e7962eb0511942f88e8122b524a64420
出典データセット
uspto-grants-2016_01
特許番号
US09238647B2

反応ノート

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