Diisopropylethylamine → HCID 69135040, compound

HRID 1828697Notes

Reaction equation

HRID 1828697 reaction equation
Br[CH2:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([C:21]([F:24])([F:23])[F:22])[CH:10]=2)=[CH:5][CH:4]=1.[CH3:27][O:28][C:29]([CH:31]1[CH2:34][NH:33][CH2:32]1)=[O:30].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:27][O:28][C:29]([CH:31]1[CH2:34][N:33]([CH2:2][C:3]2[CH:26]=[CH:25][C:6]([CH2:7][S:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:11]([C:21]([F:24])([F:23])[F:22])[CH:10]=3)=[CH:5][CH:4]=2)[CH2:32]1)=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20132751Methyl azetidine-3-carboxylateHCID 22057733HCID 22057733, compound

Product 1

HCID 69135040HCID 69135040, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-bromomethyl-benzylsulfanyl)-2-trifluoromethyl-biphenyl (185 mg, 0.4230 mmol, 1 eq.) in anhydrous DCM (7 mL) is added azetidine-3-carboxylic acid methyl ester (HCl salt, 96 mg, 0.6345 mmol, 1.5 eq.) and DIEA (0.74 mL, 4.230 mmol, 10 eq.). The mixture is stirred at room temperature for 3 h. The reaction mixture is applied directly to silica gel chromatography (gradient from 5:1 hexanes/EtOAc to 1:2 hexanes/EtOAc) to give 1-[4-(2-trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-benzyl]-azetidine-3-carboxylic acid methyl ester.

Sources & evidence

ORD record
ord-3a6f0ca7bbf4426eb9022c6adba00ed8
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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