Triethylamine → HCID 67326279, compound

HRID 1712217Notes

Reaction equation

HRID 1712217 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([P:9]([C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=2)[C:10]2[N:15]=[C:14]([NH2:16])[CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>ClCCl>[CH3:8][C:6]1[CH:5]=[C:4]([P:9]([C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=2)[C:10]2[N:15]([C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[CH:14]([NH2:16])[CH:13]=[CH:12][CH:11]=2)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 86761170HCID 86761170, compound

Product 1

HCID 67326279HCID 67326279, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bis(3,5-dimethylphenyl)phosphino-2-aminopyridine (0.19 g, 0.58 mmol) in dichloromethane (45 mL) at 0° C., triethylamine (152 μL, 1.1 mmol) and pivaloyl chloride (107 μL, 0.87 mmol) are added consecutively. The solution is slowly warmed to ambient temperature, stirred for 40 hours, and concentrated under reduced pressure. The remaining suspension is stirred with activated charcoal (0.25 g) and filtered through a Celite pad. The filtrate is concentrated under reduced pressure and the white residue is purified by column chromatography to yield 6-bis(3,5-dimethylphenyl)phosphino-N-pivaloyl-2-aminopyridine (0.16 g, 65%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. stirringThe remaining suspension is stirred with activated charcoal (0.25 g)
  3. filtrationfiltered through a Celite pad
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe white residue is purified by column chromatography

Sources & evidence

ORD record
ord-c3693d02d0524bee803f630837f97ef6
Source dataset
uspto-grants-2010_09
Patent number
US07790932B1

Reaction notes

Loading…