2,6-Lutidine → HCID 71075179, compound

HRID 1851886Notes

Reaction equation

HRID 1851886 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]4[C:31]([C:36]([O:38]C(C)(C)C)=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:26][CH:25]=2)[C:18]([CH3:43])=[C:17]3[CH3:44])=[O:13])[CH3:10])=[CH:5][CH:4]=1.N1C(C)=CC=CC=1C.[Si](OS(C(F)(F)F)(=O)=O)(CC)(CC)CC>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]4[C:31]([C:36]([OH:38])=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:26][CH:25]=2)[C:18]([CH3:43])=[C:17]3[CH3:44])=[O:13])[CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 71075164HCID 71075164, compound

Product 1

HCID 71075179HCID 71075179, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-tert-butyl 4′-((5-(1-(4-methoxyphenyl)ethylcarbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)biphenyl-2-carboxylate (58.9 mg, 0.1 mmol) and 2,6-lutidine (0.13 mL, 1.15 mmol) in DCM (1 mL) at 0° C. was added TESOTf (0.17 mL, 0.75 mmol). The reaction mixture was stirred at rt for 2 h. The completion of the reaction was monitored by anal. HPLC. The mixture was evaporated in vacuo to obtain the crude which was purified by prep. HPLC (MeOH/Acetonitrile/water) to obtain the title compound. ESI-MS (m/z): 533 [M+H]+.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto obtain the crude which
  3. customwas purified by prep

Sources & evidence

ORD record
ord-317f01fd7b6b48fd9667831eff03f6b2
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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