Chloroform → tert-Butyl 5-bromonicotinate

HRID 545204Notes

Reaction equation

HRID 545204 reaction equation
[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]

Participants

6

Reactant 3

HCID 6212Chloroform2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 887075-Bromonicotinic acid

Product 1

HCID 18422124tert-Butyl 5-bromonicotinate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6386tert-ButanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f0d2641d1576477b8765ef3cd9aa53da
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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