Sodium → [4-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)phenoxy]acetic acid tert-butyl ester

HRID 349458Notes

Reaction equation

HRID 349458 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[CH:10])=[CH:4][CH:3]=1.[C:11]([O:15][C:16](=[O:38])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[N:30]=[N:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33](Br)[CH:32]=3)=[N:27]2)=[CH:21][CH:20]=1)([CH3:14])([CH3:13])[CH3:12].[Na]>>[C:11]([O:15][C:16](=[O:38])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[N:30]=[N:29][C:28]([C:31]3[CH:32]=[CH:33][CH:34]=[C:35]([C:10]#[C:9][CH2:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH:36]=3)=[N:27]2)=[CH:21][CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 3

HCID 5360545SodiumHCID 105586681-Fluoro-4-prop-2-ynyl-benzeneHCID 68979257{4-[5-(3-Bromophenyl)tetrazol-2-ylmethyl]phenoxy}acetic acid tert-butyl ester

Product 1

HCID 68980311[4-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)phenoxy]acetic acid tert-butyl esterYield 68.9%

Procedure

This reaction was carried out as described in Example D1, Step (c) using 1-fluoro-4-prop-2-ynyl-benzene (0.23 g, 1.7 mmol) and {4-[5-(3-bromophenyl) tetrazol-2-ylmethyl]phenoxy}acetic acid tert-butyl ester (0.30 g, 0.67 mmol) in place of 4-[5-(3-bromophenyl)tetrazol-2-ylmethyl]-benzenesulfonic acid, sodium salt. This afforded 0.23 g of the product (68.5% yield).

Sources & evidence

ORD record
ord-4f5602c246744c538e36d420772251ef
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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