Tri-o-tolylphosphine → 1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 1-(phenylsulfonyl)-5-(2-thienyl)-

HRID 1432327Notes

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]#[N:21])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Sn](CCCC)(CCCC)[C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)CCC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CC#N.CC#N.Cl[Pd]Cl.C1(C)C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)[CH:18]=[C:13]3[C:12]([C:20]#[N:21])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 8 (50.0 mg, 0.128 mmol), 2-(tributylstannyl)thiophene (88 μL, 0.276 mmol), dichlorobis(acetonitrile)palladium (II) (4.0 mg, 0.0138 mmol), tri-o-tolylphosphine (8.0 mg, 0.0276 mmol) and toluene (1.0 mL) were heated at 90° C. overnight. The mixture was separated by PTLC using ethyl acetate:hexane (3:7) as eluent to give 11 as a white solid (18.3 mg, 36%); 1H NMR (400 MHz, CDCl3) δ 8.80 (d, J=2.1 Hz, 1H), 8.28 (m, 3H), 8.16 (d, J=2.1 Hz, 1H), 7.68 (tt, J=7.5, 1.2 Hz, 1H), 7.57 (t, J=4.1 Hz, 2H), 7.37 (m, 2H), 7.13 (dd, J=5.1, 3.6 Hz, 1H).

Workup

customThe mixture was separated by PTLC

Sources & evidence

ORD record: ord-8bad412eb06445f5af18eb27604c9149
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612086B2

Reaction notes

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