Chloroform → tert-Butyl 5-bromonicotinate

HRID 420152Notes

Reaction equation

HRID 420152 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, 10 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-bf2b2b15bae24a3d994beb7263d6c2e6
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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