Sodium Carbonate → Ethyl 5-cyclopropyl-2-ethoxy-6-(4-fluorophenyl)nicotinate

HRID 531034ノート

反応式

HRID 531034 の反応式
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]([O:13][CH2:14][CH3:15])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH:23]1(B(O)O)[CH2:25][CH2:24]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH:23]1([C:2]2[C:3]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:4][C:5]([O:13][CH2:14][CH3:15])=[C:6]([CH:12]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:25][CH2:24]1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 90424072Ethyl 5-bromo-2-ethoxy-6-(4-fluorophenyl)nicotinate

生成物 1

HCID 117992471Ethyl 5-cyclopropyl-2-ethoxy-6-(4-fluorophenyl)nicotinate収率 96%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

Tris(dibenzylideneacetone)dipalladium(0) (418 mg) was added to a mixture of ethyl 5-bromo-2-ethoxy-6-(4-fluorophenyl)nicotinate (2.40 g), cyclopropylboronic acid (1.68 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (401 mg), a 2 M aqueous sodium carbonate solution (9.78 mL), and toluene (25 mL), and the resultant mixture was stirred at 100° C. for 2 hours in an argon atmosphere. The reaction mixture was allowed to cool to room temperature and poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (2.06 g).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-1c09d0dcb3014bd386e575f6feca73a9
出典データセット
uspto-grants-2016_05
特許番号
US09353108B2

反応ノート

読み込み中…