Sodium Carbonate → HCID 67051395, compound

HRID 2114049Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Li+].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:18]=[C:13]3[C:12]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of the iodide 27 (2.00 g, 3.62 mmol) in toluene (40 mL) and EtOH (40 mL) was added lithium chloride (0.46 g, 10.86 mmol), dichlorobis(triphenylphosphine) palladium (II) (0.127 g, 0.18 mmol), phenylboronic acid (0.662 g, 5.43 mmol) and 1 M sodium carbonate (9.05 mL, 9.05 mmol). The mixture was refluxed under N2 (oil bath temp. 105° C.) for 2.5 h and then concentrated in vacuo. The resulting residue was co-evaporated once from xylene and purified by silicagel chromatography (gradient elution, hexanes to dichloromethane) to afford the azaindole 28 (1.16 g, 64%) as pale yellow solid. 1H NMR (400 MHz; CDCl3) δ6.91-6.94 (m, 2H), 7.04-7.08 (m, 2H), 7.22-7.30 (m, 3H), 7.31-7.41 (m, 4H), 7.44-7.53 (m, 5H), 7.60 (tt, J=7.4, 1.3 Hz, 1H), 7.87 (s, 1H), 8.23-8.26 (m, 3H) and 8.66 (d, J=1.9 Hz, 1H).

Workup

concentrationconcentrated in vacuo
custompurified by silicagel chromatography (gradient elution, hexanes to dichloromethane)

Sources & evidence

ORD record: ord-ad3652f980c640ba848f980822935351
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432375B2

Reaction notes

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