Diisopropylethylamine → HCID 86707737, compound

HRID 877428Notes

Reaction equation

HRID 877428 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) at room temperature. After 1 hour, the reaction mixture was partitioned between H2O and DCM. The organic phase was washed with saturated NH4Cl, H2O, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give Compound B26a (10 g, 65% yield). HPLC: RT=1.6 (LCMS Method Q). MS (ES): m/z=321.9 [M+H]+. 1H NMR (500 MHz, CHLOROFORM-d) 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. washThe organic phase was washed with saturated NH4Cl, H2O
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give Compound B26a (10 g, 65% yield)
  7. customRT=1.6 (LCMS Method Q)

Sources & evidence

ORD record
ord-c6b6f445591a4609b16622a3a40ab19f
Source dataset
uspto-grants-2015_03
Patent number
US08987314B2

Reaction notes

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