Acetic Acid → Ethyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917750ノート

反応式

HRID 917750 の反応式
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([NH:6][C:7]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9](Cl)C=2)=[C:4]([F:21])[CH:3]=1.COS(OC)(=O)=O.C(N(CC)CC)C.CC(O)=O.[CH3:40][CH2:41][OH:42]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([NH:6][C:7]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]([CH3:9])[C:41](=[O:42])[CH:40]=2)=[C:4]([F:21])[CH:3]=1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 702EthanolHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 23630707Ethyl 4-(4-bromo-2-fluoroanilino)-6-chloronicotinate

生成物 1

HCID 23631004Ethyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate収率 77%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Ethyl 4-(4-bromo-2-fluoroanilino)-6-chloronicotinate was dissolved in CHCl3 and reacted with Me2SO4, followed by triethylamine, AcOH and EtOH as described for example 33, step B. Purification by recrystallisation (EtOAc/Hexane) gave ethyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (77%); m.p. (EtOAc/Hexane) 159-162° C. 1H NMR [400 MHz, CDCl3] δ 9.34 (br s, 1H), 8.22 (s, 1H), 7.36-7.25 (m, 3H), 5.85 (s, 1H), 4.35 (q, J=7.1 Hz, 2H), 3.54 (s, 3H), 1.39 (t, J=7.1 Hz, 3H). LCMS (APCI−) 369 (100%), 367 (100%). Anal. Calcd for C15H14BrFN2O3: C, 48.8; H, 3.8; N, 7.6. Found C, 49.1; H, 3.8; N, 7.4.

後処理

  1. customPurification
  2. customby recrystallisation (EtOAc/Hexane)

出典と根拠

ORDレコード
ord-201daaa78d8843eab8bf20687def53db
出典データセット
uspto-grants-2007_09
特許番号
US07273877B2

反応ノート

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