Sodium Carbonate → 1-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)-N-(6'-methoxy-2',3,4-trimethyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide

HRID 869943ノート

反応式

HRID 869943 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[C:4]([CH3:25])[C:3]=1[CH3:26].[CH3:27][O:28][C:29]1[N:34]=[C:33]([CH3:35])[C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:21][C:19]1([F:22])[O:18][C:17]2[CH:23]=[CH:24][C:14]([C:11]3([C:9]([NH:8][C:6]4[N:7]=[C:2]([C:32]5[C:33]([CH3:35])=[N:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=5)[C:3]([CH3:26])=[C:4]([CH3:25])[CH:5]=4)=[O:10])[CH2:13][CH2:12]3)=[CH:15][C:16]=2[O:20]1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 674874826-Methoxy-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 89228784HCID 89228784、化合物

生成物 1

HCID 710530381-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)-N-(6'-methoxy-2',3,4-trimethyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide収率 53.5%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To N-(6-chloro-4,5-dimethylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (70 mg, 0.18 mmol), 6-methoxy-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (69 mg, 0.27 mmol) and tetrakis(triphenylphosphine)-palladium (0) (21 mg, 0.018 mmol) in 1,2-dimethoxyethane (2.0 mL), 2 M Na2CO3 (276 μL, 0.55 mmol) was added. The reaction mixture was stirred and heated at 80° C. for 20 hours under N2 atmosphere. The reaction mixture was diluted with ethyl acetate (5 mL), dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane) to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6′-methoxy-2′,3,4-trimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (45 mg, 52%). ESI-MS m/z calc. 467.5. found 468.3 (M+1)+. Retention time 1.80 minutes.

後処理

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-e9571594a02d46f784c943e065c09474
出典データセット
uspto-grants-2015_03
特許番号
US08969386B2

反応ノート

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