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

HRID 2036636

반응식

HRID 2036636 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-912c0b745a454fa8af239329721693bd
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575183B2

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