Water → HCID 66813185, compound

HRID 333829Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([C:18]([OH:33])([C:29]([F:32])([F:31])[F:30])[CH:19]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=3[Cl:28])[CH3:20])[CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].I[CH2:35][CH3:36].O>CN(C=O)C.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[C:16]([C:18]([OH:33])([C:29]([F:30])([F:31])[F:32])[CH:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:35][CH3:36])=[CH:23][C:22]=3[Cl:28])[CH3:20])[CH:15]=[CH:14][N:13]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

4′-[2-(2-Chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester (Step 1, 31 mg) and silver carbonate (18 mg) in DMF (1 mL), were reacted with iodoethane (0.006 mL) and stirred at 80° C. for 17 h. The reaction mixture was poured into water (10 mL), and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash chromatography (4 g silica gel, heptane/ethyl acetate 2/1) to give the title compound as amorphous colorless solid (21 mg). MS (m/e)=515.3 (MH+).

Workup

extractionextracted twice with ethyl acetate
washThe combined organic phases were washed with brine
dry with materialdried over MgSO4
customevaporated in vacuo
customThe residue was purified by flash chromatography (4 g silica gel, heptane/ethyl acetate 2/1)

Sources & evidence

ORD record: ord-d543408737d54aaa97b0700be7dc5481
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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