Ethyl Acetate → [2-amino-5-(1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone

HRID 1784881ノート

反応式

HRID 1784881 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10].CC1(C)C(C)(C)OB([C:25]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:26]=2[CH:27]=[CH:28][N:29]3[Si](C(C)C)(C(C)C)C(C)C)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(OCC)(=O)C>O1CCOCC1.CN(C=O)C.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)C1C=CC=CC=1C1C=CC=CC=1N(C)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:25]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:26]=2[CH:27]=[CH:28][NH:29]3)=[CH:4][C:3]=1[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 27955744-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indoleHCID 13549722(2-Amino-5-bromophenyl)(pyridin-3-yl)methanone

生成物 1

HCID 15603495[2-amino-5-(1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone

試薬・触媒・溶媒 3

HCID 178482708HCID 178482708、化合物触媒HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To (2-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.120 g, 0.43 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (0.210 g, 0.52 mmol) in 1 mL of dioxane and 0.5 mL of DMF was added chloro(di-2-norbornylphosphino)(2′-dimethylamino-1,1′-biphenyl-2-yl)palladium (II) and 2M aqueous K3PO4 (0.5 mL, 1 mmol). The resulting reaction mixture was heated at 120° C. for 1 h. Ethyl acetate was then added to the reaction mixture and the organic phase was washed with water and brine, dried, filtered and concentrated. The crude product was purified by preparative TLC to afford [2-amino-5-(1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone. 1H NMR (400 MHz, CD3OD): δ 8.82 (s, 1H), 8.63 (d, J=4.9 Hz, 1H), 8.03 (d, J=7.8 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.63 (d, J=2.1 Hz, 1H), 7.47 (dd, J=7.8, 5.0 Hz, 1H), 7.30 (d, J=8.0 Hz, 1H), 7.21 (d, J=3.2 Hz, 1H), 7.10 (t, J=7.7 Hz, 1H), 6.97-6.93 (m, 2H), 6.48 (d, J=3.3 Hz, 1H).

後処理

  1. customThe resulting reaction mixture
  2. washthe organic phase was washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative TLC

出典と根拠

ORDレコード
ord-02f972cc0f5e4e0294a06273c791e05b
出典データセット
uspto-grants-2009_03
特許番号
US07504401B2

反応ノート

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