Triethylamine → Tert-butyl 2-(6-(4-(diethoxyphosphoryl)phenyl)pyridin-3-yl)propan-2-ylcarbamate

HRID 1525321Notes

Reaction equation

HRID 1525321 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[PH:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28].CCN(CC)CC>C1(C)C=CC=CC=1.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]>[CH2:27]([O:26][P:25]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)([O:29][CH2:30][CH3:31])=[O:32])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 89462588Tert-butyl 2-(6-(4-bromophenyl)pyridin-3-yl)propan-2-ylcarbamate2×HCID 178476833HCID 178476833, compound

Product 1

HCID 89463030Tert-butyl 2-(6-(4-(diethoxyphosphoryl)phenyl)pyridin-3-yl)propan-2-ylcarbamateYield 92.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 2-(6-(4-bromophenyl)pyridin-3-yl)propan-2-ylcarbamate, 33-f, (850 mg, 2.17 mmol) in toluene (15 ml) was added diethyl phosphonate (900 mg, 6.52 mmol) and Et3N (660 mg, 6.52 mmol) and PdCl2(dppf) (85 mg) under N2, and the reaction mixture was refluxed for 8 hours. The reaction solution was then evaporated and diluted with EtOAc. The organic phase was washed with brine, dried and concentrated. Purified by silica gel (DCM-DCM:MeOH=50:1) to give tert-butyl 2-(6-(4-(diethoxyphosphoryl)phenyl)pyridin-3-yl)propan-2-ylcarbamate (900 mg, 92.4%).

Workup

  1. temperaturethe reaction mixture was refluxed for 8 hours
  2. customThe reaction solution was then evaporated
  3. additiondiluted with EtOAc
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customPurified by silica gel (DCM-DCM:MeOH=50:1)

Sources & evidence

ORD record
ord-23a5d268f39c4186a9b296484f4e5728
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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