Triethylamine → Diethyl (5-{[(tert-butoxycarbonyl)amino](phenyl)methyl}pyridin-2-yl)phosphonate

HRID 1525217Notes

Reaction equation

HRID 1525217 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH:8]([C:15]1[CH:16]=[N:17][C:18](Br)=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[P:23]([O-:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26].CCN(CC)CC>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6]([NH:7][CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:20]=[CH:19][C:18]([P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[N:17][CH:16]=1)=[O:22])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 131733138tert-Butyl[(6-bromopyridin-3-yl)(phenyl)methyl]carbamate

Product 1

HCID 131733137Diethyl (5-{[(tert-butoxycarbonyl)amino](phenyl)methyl}pyridin-2-yl)phosphonateYield 86%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl (6-bromopyridin-3-yl)(phenyl)methylcarbamate (4-e) (3.4 g, 9.4 mmol), diethyl phosphite (1.55 g, 11.27 mmol) and Et3N (1.14 g, 11.27 mmol) in THF was added PdCl2(dppf) (200 mg). The mixture was heated at reflux under nitrogen overnight. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified over silica gel (DCM/MeOH=20/1) to provide the product, 4-f (3.4 g, 86%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen overnight
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified over silica gel (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-5ef3b9b7d63240faab60b022c60e09a2
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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