Cesium carbonate → 2-(5-fluoropyridin-3-ylamino)-N-methyl-3-nitrobenzamide

HRID 2036636

反応式

HRID 2036636 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:50]1[C:59]([N+:60]([O-:62])=[O:61])=[CH:58][CH:57]=[CH:56][C:51]=1[C:52]([NH:54][CH3:55])=[O:53].[F:63][C:64]1[CH:65]=[C:66]([NH2:70])[CH:67]=[N:68][CH:69]=1>C1(C)C=CC=CC=1.CCOC(C)=O.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]>[F:63][C:64]1[CH:65]=[C:66]([NH:70][C:50]2[C:59]([N+:60]([O-:62])=[O:61])=[CH:58][CH:57]=[CH:56][C:51]=2[C:52]([NH:54][CH3:55])=[O:53])[CH:67]=[N:68][CH:69]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 5744505-Fluoro-3-pyridinamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 674334472-bromo-N-methyl-3-nitrobenzamide

生成物 1

HCID 674327582-(5-fluoropyridin-3-ylamino)-N-methyl-3-nitrobenzamide

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of cesium carbonate (1.55 g, 4.75 mmol), xantphos (550 mg, 0.950 mmol), 2-bromo-N-methyl-3-nitrobenzamide (820 mg, 3.17 mmol) (Prepared in Example 20), tris(dibenzylideneacetone)dipalladium (0) (580 mg, 0.63 mmol), 5-fluoropyridin-3-amine (532 mg, 4.75 mmol) in toluene (15 mL) under N2 was heated at 100° C. for 18 h. The mixture was cooled to rt and diluted with EtOAc. The mixture was filtered and the filtrates were concentrated in vacuo. Purification of the residue by flash chromatography over silica gel, using EtOAc as eluent gave 2-(5-fluoropyridin-3-ylamino)-N-methyl-3-nitrobenzamide: 1H NMR (400 MHz, CDCl3) δ 9.29 (1H, s), 8.23 (1H, s), 8.21 (1H, d, J=8.0 Hz), 8.16 (1H, s), 7.89 (1H, d, J=8.0 Hz), 7.26 (1H, t, J=8.0 Hz), 7.04 (1H, d, J=8.0 Hz), 6.41 (1H, br), 2.78 (3H, d, J=4.0 Hz); LC-MS (ESI) m/z 291.1 [M+H]+.

後処理

  1. temperatureThe mixture was cooled to rt
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrates were concentrated in vacuo
  4. customPurification of the residue by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-912c0b745a454fa8af239329721693bd
出典データセット
uspto-grants-2013_11
特許番号
US08575183B2

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