Diisopropylethylamine → HCID 86707737, compound

HRID 1190845Notes

Reaction equation

HRID 1190845 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.Cl[C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH:6][C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 6101914-Bromo-2,6-difluoroaniline

Product 1

HCID 86707737HCID 86707737, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2,6-difluoroaniline (10 g, 48 mmol) in DCM (15 mL) was added ethyl 3-chloro-3-oxopropanoate (6.8 mL, 53 mmol) and DIEA (9.2 mL, 53 mmol) and the reaction mixture stirred for 1 h. The reaction mixture was partitioned between H2O and DCM and the layers separated. The DCM portion was washed with satd. NH4Cl and H2O then dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure to give Compound 90a (10 g, 65% yield). LCMS=1.60 min using analytical method (Q), 321.9 (M+H). 1H NMR (500 MHz, CDCl3) δ 8.89 (br. s., 1H), 7.20-7.15 (m, 2H), 4.29 (q, J=7.2 Hz, 2H), 3.54 (s, 2H), 1.36-1.31 (m, 3H).

Workup

  1. customThe reaction mixture was partitioned between H2O and DCM
  2. customthe layers separated
  3. washThe DCM portion was washed with satd
  4. dry with materialNH4Cl and H2O then dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9b6351efb64e45e88eafe74588515521
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

Loading…