Triethylamine → HCID 20607510, compound

HRID 431374Notes

Reaction equation

HRID 431374 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12](Br)[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1B(O)O.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([C:18]2[CH:17]=[CH:16][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 20607510HCID 20607510, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromoisophthalic acid dimethylester (544 mg, 2 mmol), 2-naphthaleneboronic acid (342 mg, 2 mmol), Pd(OAc)2 (8 mg), tri-o-tolylphosphine (30 mg) and 5 ml Et3N (5 ml) in 10 ml DMF was stirred at 100° C. for overnight The reaction mixture was purified by silica gel column eluted by 20% EtAc in hexane to afford the product (75% yield). 1H NMR (Acetone-d6, 400 MHz), 8.55 (s, 1H), 8.45 (s, 2H), 8.17 (d, 1H), 7.91 (d, 1H), 7.88 (d, 1H), 7.77 (t, 1H), 7.67 (t, 1H), 7.38 (m, 2H), 4.03 (s, 6H).

Workup

  1. customwas purified by silica gel column
  2. washeluted by 20% EtAc in hexane

Sources & evidence

ORD record
ord-7c110c8093c34a54b0ca665de0b16b1f
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

Loading…