Diisopropylethylamine → HCID 53640738, compound

HRID 1695955Notes

Reaction equation

HRID 1695955 reaction equation
[Br:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C1CN([P+]([O:28][N:29]2N=NC3C=CC=C[C:30]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:45]CN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:29]([O:28][CH3:45])[CH3:30])=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3026222-Bromo-3-fluorobenzoic acidHCID 2724699PyBOP

Product 1

HCID 53640738HCID 53640738, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-3-fluorobenzoic acid (9.27 g), 1-N,O-dimethylhydroxylamine hydrochloride (4.129 g, 42.33 mmol), and PyBOP (22.03 g, 1 eq., 42.33 mmol) were suspended in DCM (400 mL). DIEA was then added and the resulting solution was stirred at room temp. for 14 h (no SM left by TLC). The solution was then washed with water, IN aq HCl and aq sat. NaHCO3 in succession. The organics were dried (MgSO4) and concentrated in vacuo. The residue was purified by ISCO (330 g SiO2, attached) to give 8.3 g (75%) of 2-bromo-3-fluoro-N-methoxy-N-methylbenzamide as a white solid. Rf˜0.5 (1:1 Hex:EtOAc); LC/MS ES+1: 261.99.

Workup

  1. waitleft by TLC)
  2. washThe solution was then washed with water, IN aq HCl
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by ISCO (330 g SiO2, attached)

Sources & evidence

ORD record
ord-7d9a6771c9bc47d182efd5b649334c79
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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