Potassium Carbonate → 6-Amino-4-(cyclohexyloxy)-2-methylnicotinonitrile

HRID 928389ノート

反応式

HRID 928389 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]#[N:10])=[C:4]([O-:11])[CH:3]=1.[Na+].C([O-])([O-])=O.[K+].[K+].[C:19]1(Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([O:11][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:5]([C:9]#[N:10])=[C:6]([CH3:8])[N:7]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 5197751-Bromocyclohex-1-eneHCID 58081220Sodium 6-amino-3-cyano-2-methylpyridin-4-olate

生成物 1

HCID 667236456-Amino-4-(cyclohexyloxy)-2-methylnicotinonitrile

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of sodium 6-amino-3-cyano-2-methylpyridin-4-olate (300 mg, 1.75 mmol) and K2CO3 (485 mg, 3.51 mmol) in DMF (6 ml) was added Cyclohexenylbromide (0.213 ml, 1.84 mmol) and the reaction mixture was stirred at it for 14 h. NaHCO3 (100 ml) was added and the mixture was extracted with EA (5×30 ml). The combined organic extracts were dried over Na2SO4, filtered and concentrated. The resulting product was dissolved in n-PrOH (10 ml), and hydrogenated (1 atm H2, rt) for 1 h over Pd/C (93 mg, 0.088 mmol). The reaction mixture was filtered and the filtrate was adsorbed on celite. Purification by column chromatography (CombiFlash Companion, 10 g SiO2, DCM to DCM:MeOH 9:1) afforded the desired product. LCMS RtM=1.63 min, [M+H]+=232.6.

後処理

  1. extractionthe mixture was extracted with EA (5×30 ml)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe resulting product was dissolved in n-PrOH (10 ml)
  6. filtrationThe reaction mixture was filtered
  7. customPurification by column chromatography (CombiFlash Companion, 10 g SiO2, DCM to DCM:MeOH 9:1)

出典と根拠

ORDレコード
ord-2c8382e268a14b8d9205c5761e0fd2fa
出典データセット
uspto-grants-2016_03
特許番号
US09290485B2

反応ノート

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