Sodium Carbonate → N-[4-Methyl-3-(3-methyl-1,2-benzisoxazol-6-yl)phenyl]-2-pyrrolidin-1-ylisonicotinamide

HRID 1988912ノート

反応式

HRID 1988912 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[CH:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:32])[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:22]=2)=[CH:15][C:14]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:32])[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:22]=2)=[CH:15][C:14]=1[C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 11258289N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-2-pyrrolidin-1-yl-isonicotinamide2 回HCID 124113226-Bromo-3-methyl-1,2-benzoxazole

生成物 1

HCID 10364356N-[4-Methyl-3-(3-methyl-1,2-benzisoxazol-6-yl)phenyl]-2-pyrrolidin-1-ylisonicotinamide収率 36.9%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 6-bromo-3-methyl-1,2-benzisoxazole (11 mg), N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-pyrrolidin-1-yl-isonicotinamide (Intermediate 13, 15 mg) and aqueous sodium carbonate (0.5M, 0.25 ml) in anhydrous DME (1 ml) was degassed then stirred under nitrogen. A solution of tetrakis(triphenylphosphine)palladium(0) (2.5 mg) in DME (0.25 ml) was added and the mixture was stirred at 80° for 16 h. The solvent was removed under vacuum and the residue was partitioned between dichloromethane and water. The organic layer was separated using a hydrophobic filter, the solvent was evaporated and the residue was purified by column chromatography on silica, eluting with a cyclohexane-ethyl acetate gradient to give the title compound as an oil (5.6 mg).

後処理

  1. customwas degassed
  2. additionA solution of tetrakis(triphenylphosphine)palladium(0) (2.5 mg) in DME (0.25 ml) was added
  3. stirringthe mixture was stirred at 80° for 16 h
  4. customThe solvent was removed under vacuum
  5. customthe residue was partitioned between dichloromethane and water
  6. customThe organic layer was separated
  7. customthe solvent was evaporated
  8. customthe residue was purified by column chromatography on silica
  9. washeluting with a cyclohexane-ethyl acetate gradient

出典と根拠

ORDレコード
ord-f9307f2e331f4519a496d917cb278383
出典データセット
uspto-grants-2010_01
特許番号
US07642276B2

反応ノート

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