Cesium carbonate → HCID 66690540, 화합물

HRID 592289노트

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HRID 592289 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 66690540HCID 66690540, 화합물수율 57.7%

시약·촉매·용매 3

HCID 53485975CID 53485975촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e7962eb0511942f88e8122b524a64420
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238647B2

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