Potassium Phosphate, Tribasic → HCID 86728224、化合物

HRID 1776794ノート

反応式

HRID 1776794 の反応式
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.C(OC([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1B(O)O)=O)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:10][C:4]1[N:3]=[C:2]([C:19]2[NH:18][C:26]3[C:21]([CH:20]=2)=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:7]([O:8][CH3:9])=[CH:6][CH:5]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 717433362,6-Dichloro-3-methoxypyridine

生成物 1

HCID 86728224HCID 86728224、化合物収率 69.8%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a degassed solution of compound 2,6-dichloro-3-methoxypyridine (8.9 g, 0.05 mol), (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (13 g, 0.05 mol) and K3PO4 (31.8 g, 3.0 mol) in DMF (100 mL) was added Pd(dppf)Cl2 (3.65 g, 5 mmol) under N2. The mixture was heated at 60° C. for about 15 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc and filtered. The filtrate was washed with H2O, brine, dried over Na2SO4. After being concentrated in vacuo, the resulting resulting residue was purified using prep-HPLC to provide the desired product of 2-(6-chloro-3-methoxypyridin-2-yl)-1H-indole (9.0 g, yield: 69.8%). 1H-NMR (CDCl3, 400 MHz) δ 9.52 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.38˜7.43 (m, 2H), 7.07˜7.26 (m, 4H), 4.03 (s, 3H). MS (M+H)+: 259/261.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter being concentrated in vacuo
  6. customthe resulting resulting residue
  7. customwas purified

出典と根拠

ORDレコード
ord-3f9a02eb11a747078ca15bfd777101a4
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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