Tri-o-tolylphosphine → HCID 59812182, compound

HRID 2114053Notes

Reaction equation

HRID 2114053 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[C:12]([C:20]3[CH:24]=[CH:23][O:22][CH:21]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Sn](CCCC)(CCCC)[C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)CCC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.Cl[Pd]Cl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)[CH:18]=[C:13]3[C:12]([C:20]3[CH:24]=[CH:23][O:22][CH:21]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 9978492HCID 9978492, compound

Product 1

HCID 59812182HCID 59812182, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of bromide 30 (40.3 mg, 0.1 mmol), tributylthiophen-2-yl-stannane (62 μL, ca 0.2 mmol), PdCl2.(MeCN)2 (3.6 mg, 0.014 mmol), and tri-o-tolyl-phosphane (6.6 mg, 0.022 mmol) in toluene (0.9 mL) was stirred under N2 for 2 h. The reaction mixture was cooled and separated by PTLC with CH2Cl2 as eluent to afford 33 (31.7 mg, 78%) as yellowish solid. 1H NMR (400 MHz; CDCl3) δ 6.71 (dd, J=2.0, 1.0 Hz, 1H), 7.12 (dd, J=5.1, 3.6 Hz, 1H), 7.32 (dd, J=3.6, 1.2 Hz, 1H), 7.35 (dd, J=5.1, 1.2 Hz, 1H), 7.48-7.63 (m, 4H), 7.82 (m, 1H), 7.84 (s, 1H), 8.09 (d, J=2.2 Hz, 1H), 8.22-8.26 (m, 2H), 8.73 (d, J=2.2 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customseparated by PTLC with CH2Cl2 as eluent

Sources & evidence

ORD record
ord-5b48719925c0403db73f36bf623508b1
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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