Triethylamine → 4-bromo-N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-butanamide

HRID 630407Notes

Reaction equation

HRID 630407 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:16]([O:17][CH3:18])=[CH:15][C:13]([NH2:14])=[C:12]([Cl:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32].C(OCC)(=O)C>O1CCCC1>[Br:27][CH2:28][CH2:29][CH2:30][C:31]([NH:14][C:13]1[CH:15]=[C:16]([O:17][CH3:18])[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:11][C:12]=1[Cl:19])=[O:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 702254-Bromobutyryl chlorideHCID 671456574-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline2×

Product 1

HCID 866772174-bromo-N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-butanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline (intermediate 39; 0.75 g, 2.48 mmol) in tetrahydrofuran (20 mL) and triethylamine (0.38 mL, 2.73 mmol) was added under nitrogen atmosphere at 0° C. 4-bromobutanoyl chloride (0.32 mL, 2.76 mmol). The mixture was stirred for half an hour. Ethyl acetate was added to the mixture and the organic layer was washed with bicarbonate and brine, dried and the solvent was removed under reduced pressure. The title compound was obtained (97%) and it was used in the next step without further purification.

Workup

  1. washthe organic layer was washed with bicarbonate and brine
  2. customdried
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-191337b7391a43d0825edefa616fc92a
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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