Potassium Carbonate → (3'-Methoxy-[4,4]bipyridinyl-3-yl)-methyl-amine

HRID 878051ノート

反応式

HRID 878051 の反応式
C[N:2]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1N1CCCCC1C)[C:3](=O)C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1.[CH3:32][O:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][C:39]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.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>[CH3:32][O:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][C:39]=1[C:24]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[NH:2][CH3:3]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 467390193-Methoxypyridine-4-boronic acidHCID 86670691N-Methyl-N-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-3,5-bis-trifluoromethyl-benzamide2 回

生成物 1

HCID 70663638(3'-Methoxy-[4,4]bipyridinyl-3-yl)-methyl-amine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of (4-bromo-pyridin-3-yl)-methyl-amine (50 mg, 0.267 mmol, example 25, intermediate b) and 3-methoxypyridine-4-boronic acid (CAS RN 1008506-24-8) (61.35 mg, 0.4 mmol) in dry DMF (3 mL) in a sealed tube was added potassium carbonate (2.14 mmol) and the reaction mixture was purged with argon for 10 min. Then, Pd(PPh3)4 (30.89 mg, 0.03 mmol) was added and again purged with nitrogen for 15 min. The reaction mixture was heated at 100° C. for 16 hours. After cooling to room temperature the reaction mixture was filtered through a bed of celite and the filter cake washed with EtOAc. The solvent was evaporated, the residue was dissolved in EtOAc and washed with water. The organic layer was dried over sodium sulphate and evaporated to get compound that was used in next step without further purification. Brown solid (55 mg, 95%). MS (ESI): m/z=216.2 [M+H]+.

後処理

  1. customthe reaction mixture was purged with argon for 10 min
  2. customagain purged with nitrogen for 15 min
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. filtrationwas filtered through a bed of celite
  5. washthe filter cake washed with EtOAc
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in EtOAc
  8. washwashed with water
  9. dry with materialThe organic layer was dried over sodium sulphate
  10. customevaporated
  11. customto get compound that
  12. customwas used in next step without further purification

出典と根拠

ORDレコード
ord-0c0efd976bc64f48909b87bf871c39e7
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

反応ノート

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