Ethyl Bromide → 2-Ethyl-6-methylisonicotinic acid tert-butyl ester

HRID 1924822

反応式

HRID 1924822 の反応式
[CH2:1]([Mg]Br)[CH3:2].C(Br)C.[Mg].[C:9]([O:13][C:14](=[O:23])[C:15]1[CH:20]=[C:19]([CH3:21])[N:18]=[C:17](Cl)[CH:16]=1)([CH3:12])([CH3:11])[CH3:10]>CCOCC.C1COCC1.CN1C(=O)CCC1>[C:9]([O:13][C:14](=[O:23])[C:15]1[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([CH2:1][CH3:2])[CH:16]=1)([CH3:12])([CH3:11])[CH3:10]

参加物

8

反応物 4

HCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 860403662-Chloro-6-methyl-isonicotinic acid tert-butyl esterHCID 178418443HCID 178418443、化合物

生成物 1

HCID 670269672-Ethyl-6-methylisonicotinic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A solution of ethylmagnesiumbromide (freshly prepared from ethylbromide (392 mg, 3.6 mmol) and magnesium (83 mg, 3.4 mmol)) in Et2O (10 mL) is added to a cooled (−40° C.) and mechanically stirred solution of 2-chloro-6-methyl-isonicotinic acid tert-butyl ester (0.76 g, 3.34 mmol), Fe(acac)3 (21.2 mg, 0.06 mmol) and NMP (0.6 mL) in THF (60 mL). The mixture is warmed to rt during 0.5 h, diluted with Et2O (150 mL) and quenched with aq. KHSO4 (1 M, 40 mL). The phases are separated and the aq. phase is extracted with Et2O (2×50 mL). The combined organic extracts are dried (MgSO4), filtered and evaporated. The residue is purified by reversed phase MPLC to give 2-ethyl-6-methyl-isonicotinic acid tert-butyl ester; LC-MS: tR=0.67 min, [M+1]+=222.19; 1H NMR (CDCl3): δ 7.44 (s, 2H), 2.83 (q, J=7.6 Hz, 2H), 2.58 (s, 3H), 1.59 (s, 9H), 1.30 (t, J=7.6 Hz, 3H).

後処理

  1. additionis added to
  2. customquenched with aq. KHSO4 (1 M, 40 mL)
  3. customThe phases are separated
  4. extractionthe aq. phase is extracted with Et2O (2×50 mL)
  5. dry with materialThe combined organic extracts are dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by reversed phase MPLC

出典と根拠

ORDレコード
ord-c9aaad0c9712469f92d29d775a73a557
出典データセット
uspto-grants-2012_05
特許番号
US08178562B2

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