Triethylamine → Tert-butyl (2-chloro-3-fluoropyridin-4-yl)carbamate

HRID 59943Notes

Reaction equation

HRID 59943 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[Cl:18][C:19]1[C:24]([F:25])=[C:23](C(O)=O)[CH:22]=[CH:21][N:20]=1.CC[N:31]([CH2:34]C)CC.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37].C1(C)C=CC=CC=1>O>[Cl:18][C:19]1[C:24]([F:25])=[C:23]([NH:31][C:34](=[O:8])[O:40][C:36]([CH3:39])([CH3:38])[CH3:37])[CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27828122-Chloro-3-fluoropyridine-4-carboxylic acidHCID 22595558Toluene tert-butyl alcohol

Product 1

HCID 86723306Tert-butyl (2-chloro-3-fluoropyridin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Diphenylphosphoryl azide (DPPA) (129 mmol) was added to a mixture of 2-chloro-3-fluoro-pyridine-4-carboxylic acid (85.7 mmol), Et3N (257 mmol) in 1:1 tert-BuOH/toluene (200 mL). The mixture was heated at 110° C. for 4 h. Mixture was diluted with H2O and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (SiO2, 100:0 to 80:20 DCM/EtOAc) to yield the desired product tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (SiO2, 100:0 to 80:20 DCM/EtOAc)

Sources & evidence

ORD record
ord-a820ba9736f8407c87728d1a09bd069b
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Reaction notes

Loading…