Triethylamine → HCID 66805407, compound

HRID 1193284Notes

Reaction equation

HRID 1193284 reaction equation
CO[C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.C(N(CC)CC)C.Cl.[NH2:22][C@H:23]1[C:31]2[C:26](=[CH:27][C:28]([C:33]([O:35][CH3:36])=[O:34])=[C:29]([F:32])[CH:30]=2)[CH2:25][CH2:24]1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[Cl:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:22]([C@H:23]1[C:31]3[C:26](=[CH:27][C:28]([C:33]([O:35][CH3:36])=[O:34])=[C:29]([F:32])[CH:30]=3)[CH2:25][CH2:24]1)[CH2:11]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 22935208Methyl 2-(bromomethyl)-6-chlorobenzoateHCID 66798889HCID 66798889, compound

Product 1

HCID 66805407HCID 66805407, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Bromomethyl-6-chlorobenzoic acid methyl ester (1.75 mmol, 1.0 eq) was dissolved in toluene (5.3 ml) and triethylamine (3.675 mmol, 2.1 eq), and (R)-methyl 1-amino-6-fluoro-2,3-dihydro-1H-indene-5-carboxylate hydrochloride (A-05) (1.75 mmol, 1 eq) was added. The reaction mixture was refluxed for 16 h and then diluted with ethyl acetate and sat. NaHCO3 solution. The phases were separated, and the organic phase was washed with sat. NaCl solution, dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, cyclohexane:EA 2:1). Yield: 65%

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customThe phases were separated
  3. washthe organic phase was washed with sat. NaCl solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, cyclohexane:EA 2:1)

Sources & evidence

ORD record
ord-ef55e621c5ff4e4cb8ec744e7552d9eb
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…