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

HRID 1924822

반응식

HRID 1924822 반응식
[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]

참가 물질

8

반응물 4

HCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 860403662-Chloro-6-methyl-isonicotinic acid tert-butyl esterHCID 178418443HCID 178418443, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c9aaad0c9712469f92d29d775a73a557
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178562B2

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