Trimethylsilyldiazomethane → methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate

HRID 1051096Notes

Reaction equation

HRID 1051096 reaction equation
[N+](=[CH:3][Si](C)(C)C)=[N-].[F:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:23]=[C:22]3[C:18]([CH2:19][CH2:20][CH:21]3[NH:24][C:25]3[CH:26]=[C:27]([CH:33]=[CH:34][CH:35]=3)[O:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1>C1COCC1>[F:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:23]=[C:22]3[C:18]([CH2:19][CH2:20][CH:21]3[NH:24][C:25]3[CH:26]=[C:27]([CH:33]=[CH:34][CH:35]=3)[O:28][CH2:29][C:30]([O:32][CH3:3])=[O:31])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 1181615432-(3-((6-(3-Fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetic acid

Product 1

HCID 118161550methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2 M solution of (diazomethyl)trimethylsilane in THF (0.20 mL, 0.40 mmol) was added to a solution of 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetic acid (159 mg, 0.421 mmol) in THF (5 mL) at 0° C. in a 50 mL round bottom flask. The mixture was allowed to stir for 2 hours at room temperature. The resulting mixture was concentrated in vacuo and the resulting crude residue was purified on a Teledyne-Isco combiflash machine (12 g column, hexanes→100% ethyl acetate/hexanes, gradient), to afford 135 mg (82%) of methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe resulting crude residue was purified on a Teledyne-Isco combiflash machine (12 g column, hexanes→100% ethyl acetate/hexanes, gradient)

Sources & evidence

ORD record
ord-390feb889d9f42fc840423c23a6641bb
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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