Acetyl chloride → methyl 2-(3-(N-(6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)acetamido)phenoxy)acetate

HRID 1051097Notes

Reaction equation

HRID 1051097 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][CH2:13][CH:14]3[NH:17][C:18]3[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=3)[O:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.CN(C1C=CC=CN=1)C.[C:39](Cl)(=[O:41])[CH3:40].C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][CH2:13][CH:14]3[N:17]([C:18]3[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=3)[O:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:39](=[O:41])[CH3:40])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 118161550methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate

Product 1

HCID 118161545methyl 2-(3-(N-(6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)acetamido)phenoxy)acetateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate (8 mg, 0.02 mmol) and dimethylaminopyridine (2 mg, 0.016 mmol) in dichloromethane (1 mL) at 0° C. was added acetyl chloride (12 mL, 0.173 mmol) and triethylamine (0.25 mL, 0.176 mmol). The reaction was warmed to room temperature and allowed to stir for approximately 2 hours. The resultant mixture was concentrated and the resulting crude residue was purified on a preparative TLC (1000 mm thickness) with a 1:1 ratio of ethyl acetate and hexane solution to afford 7 mg (94%) of methyl 2-(3-(N-(6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)acetamido)phenoxy)acetate.

Workup

  1. concentrationThe resultant mixture was concentrated
  2. customthe resulting crude residue was purified on a preparative TLC (1000 mm thickness) with a 1:1 ratio of ethyl acetate and hexane solution

Sources & evidence

ORD record
ord-169cfd33bb9f41048ddf6a9d0ebef30c
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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