Chloroform → tert-Butyl 5-bromonicotinate

HRID 1096918노트

반응식

HRID 1096918 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].CCN=C=N[CH2:16][CH2:17][CH2:18]N(C)C.Cl.[CH:23](Cl)(Cl)Cl>C(O)(C)(C)C.CN(C1C=CN=CC=1)C>[C:17]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=1)([CH3:18])([CH3:23])[CH3:16]

참가 물질

6

반응물 3

HCID 6212Chloroform2회HCID 887075-Bromonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 18422124tert-Butyl 5-bromonicotinate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6386tert-Butanol용매

실험 절차

5-Bromo-nicotinic acid (20.2 g, 100 mmol) was dissolved in CHCl3 (200 mL) and tert-BuOH (40 mL); and WSC-HCl (21.1 g, 110 mmol) and DMAP (21.1 g, 110 mmol) was added thereto in order, and stirred at room temperature over night. The reaction mixture was diluted with chloroform, washed with 0.5N HCl aq. (220 mL), 0.5N NaOH aq. (100 mL), brine and dried over MgSO4 and silica gel. After filtration, the solvents were removed in vacuo to afford 5-Bromo-nicotinic acid tert-butyl ester as a colorless solid. This solid was used for the next step without further purification.

후처리

  1. washwashed with 0.5N HCl aq. (220 mL), 0.5N NaOH aq. (100 mL), brine
  2. dry with materialdried over MgSO4 and silica gel
  3. filtrationAfter filtration
  4. customthe solvents were removed in vacuo

출처 및 근거

ORD 기록
ord-19b3ec0465614a6396955159750c286e
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138197B2

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