Ethyl 4-iodobenzoate → HCID 9802822, compound

HRID 1955340Notes

Reaction equation

HRID 1955340 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[C:16](=[O:17])[CH:15]3[CH2:18][CH2:19][CH:12]2[CH2:13][CH2:14]3)=[CH:5][CH:4]=1)#[CH:2].I[C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1>[Cl-].C[N+](C)(C)CC1C=CC=CC=1.C(N(CC)CC)C>[O:17]=[C:16]1[CH:15]2[CH2:18][CH2:19][CH:12]([CH2:13][CH2:14]2)[N:11]1[CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:23]2[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 9795781HCID 9795781, compound

Product 1

HCID 9802822HCID 9802822, compound

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 8471TriethylamineSolvent

Procedure

In the a) route of scheme 3, compound 5 is reacted with ethyl 4-iodo-benzoate in the presence of triethylamine (Et3N), trimethyl-benzylammonium chloride (Me3N (Bn) Cl) and tetrakistriphenylphosphine palladium (Pd(PPh3)4) to give ethyl 4-[4-[3-(3-oxo-2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylethynyl]-benzoate (compound 15), then 4-[4-[3-(3-oxo-2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylethynyl]-benzoic acid (compound 16 ) is provided by hydrolysis of compound 15.

Sources & evidence

ORD record
ord-c466b451704640079e958b37f8a628fd
Source dataset
uspto-grants-2000_09
Patent number
US06124460

Reaction notes

Loading…