Chloroform → tert-Butyl 5-bromonicotinate

HRID 545204노트

반응식

HRID 545204 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.[CH:22](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])([CH3:22])[CH3:16]

참가 물질

6

반응물 3

HCID 6212Chloroform2회HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 887075-Bromonicotinic acid

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 (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-f0d2641d1576477b8765ef3cd9aa53da
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935712B2

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