Triethylamine → HCID 59380827, compound

HRID 2354135Notes

Reaction equation

HRID 2354135 reaction equation
[Br:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.ClC(OCC(C)C)=O.Cl.[CH3:27][NH:28][O:29][CH3:30]>C(Cl)Cl.O>[Br:1][C:2]1[C:3]([C:8]([N:28]([O:29][CH3:30])[CH3:27])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 20501293-Bromopyridine-2-carboxylic Acid

Product 1

HCID 59380827HCID 59380827, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromopyridine-2-carboxylic acid (3-1; 250 mg, 1.24 mmole) in CH2Cl2 (5 mL) was added Et3N (0.21 mL, 3.72 mmole) then isobutyl chloroformate (0.19 mL, 1.49 mmole) at 0° C. After 30 minutes N,O-dimethylhydroxylamine hydrochloride (181 mg, 1.86 mmole) was added. After 15 minutes the mixture was warmed to RT. After 18 hr the mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (50% EtOAc/hexanes) gave the title compound (3-2) as a clear oil: 1H-NMR (500 MHz, CDCl3) δ 8.56 (m, 1H), 7.92 (m, 1H), 7.24 (m, 1H), 3.58 (s, 3H), 3.42 (s, 3H).

Workup

  1. customat 0° C
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e626b972d540465986191aa0e7c0f519
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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