Pivaloyl chloride → HCID 13154251, compound

HRID 132370Notes

Reaction equation

HRID 132370 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:15])([CH3:14])[C:11](Cl)=[O:12]>N1C=CC=CC=1>[F:1][C:2]1[N:7]=[C:6]([NH:8][C:11](=[O:12])[C:10]([CH3:15])([CH3:14])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 27613996-Fluoropyridin-2-amine

Product 1

HCID 13154251HCID 13154251, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

6-fluoropyridin-2-amine (13.1 g, 117 mmol) was dissolved in anhydrous pyridine (100 mL), and cooled to 0° C. followed by fast dropwise addition of trimethylacetyl chloride (15.9 mL, 129 mmol) over 2 min. 5 min later, the resulting slurry was stirred over night at room temperature. Partial of the solvent was removed on rotary vacuum. The residue was partitioned between saturated ammonium chloride (200 mL) and EtOAc (200 mL). After separation, the organic layer was washed with brine (50 mL), dried over MgSO4, concentrated on rotary vacuum, and purified on flash chromatography eluting with 25˜75% EtOAc/Hexanes (1400 mL) to afford the expected product as a white solid (21.4 g, 93% yield); 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (s, 9 H), 6.63 (dd, J=8.06, 2.01 Hz, 1 H), 7.76 (q, J=8.14 Hz, 1 H), 7.85 (s, 1 H), 8.09 (dd, J=8.06, 1.76 Hz, 1 H); Mass spec. 197.15 (MH+), Calc. for C10H13FN2O196.1.

Workup

  1. customPartial of the solvent was removed on rotary vacuum
  2. customThe residue was partitioned between saturated ammonium chloride (200 mL) and EtOAc (200 mL)
  3. customAfter separation
  4. washthe organic layer was washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated on rotary vacuum
  7. custompurified on flash chromatography
  8. washeluting with 25˜75% EtOAc/Hexanes (1400 mL)

Sources & evidence

ORD record
ord-65fc9951c02545a7b71c682e48a2dac4
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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