1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 3-(6-bromopyridin-3-yl)-2-[(tert-butoxycarbonyl)amino]acrylate

HRID 449497

Reaction equation

HRID 449497 reaction equation
N12CCCN=C1CCCCC2.[Br:12][C:13]1[N:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=1.[C:21]([O:25][C:26]([NH:28][CH:29](P(OC)(OC)=O)[C:30]([O:32][CH3:33])=[O:31])=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl>[Br:12][C:13]1[N:18]=[CH:17][C:16]([CH:19]=[C:29]([NH:28][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[C:30]([O:32][CH3:33])=[O:31])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 397380Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 72307888Methyl 3-(6-bromopyridin-3-yl)-2-[(tert-butoxycarbonyl)amino]acrylateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (480 uL, 3.2 mmol) was added to a mixture of 6-bromo-pyridine-3-carbaldehyde (Aldrich, Cat. #596280) (500 mg, 3 mmol) and methyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate (Fluka, Cat. #09659) (960 mg, 3.2 mmol) in methylene chloride (5 mL) at r.t. under N2. The reaction was stirred for 2 h. The reaction was partitioned between EtOAc and 1 N HCl. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give crude methyl 3-(6-bromopyridin-3-yl)-2-[(tert-butoxycarbonyl)amino]acrylate (0.9 g, 93%) as an off white solid. Analytical LCMS (M+H)+: m/z=356.8, 358.9.

Workup

  1. customThe reaction was partitioned between EtOAc and 1 N HCl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-920f45e7c03f4cee8fae2f95d344ef49
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Linked notes

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