Water → 9-(3-Ethanesulfonyl-phenyl)-5H-pyrazino[2,3-b]indole

HRID 1882221Notes

Reaction equation

Br[C:2]1[C:3]2[C:4]3[N:14]=[CH:13][CH:12]=[N:11][C:5]=3[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1.[CH2:15]([S:17]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([S:17]([C:20]1[CH:25]=[C:24]([C:2]2[C:3]3[C:4]4[N:14]=[CH:13][CH:12]=[N:11][C:5]=4[NH:6][C:7]=3[CH:8]=[CH:9][CH:10]=2)[CH:23]=[CH:22][CH:21]=1)(=[O:18])=[O:19])[CH3:16]

Participants

Conditions

Temperature: 150 °C

Procedure

Compound 80 (50 mg, 0.2 mmol), 3-ethanesulfonyl-phenylboronic acid (65 mg, 0.3 mmol), tetrakis(triphenylphosphine)palladium (0) (116 mg, 0.1 mmol), and potassium carbonate (83 mg, 0.6 mmol), were combined in dioxane (2 mL) and H2O (0.2 mL) in a sealed tube under nitrogen. The reaction was heated at 150° C. in the microwave for 20 min and then concentrated in vacuo. Purification by silica gel chromatography (5% MeOH/CH2Cl2) gave 46 mg (68%) of the title compound as a light orange solid. 1H NMR (400 MHz, CH3OD) δ 8.42 (t, 1H, J=2.8 Hz), 8.31 (d, 1H, J=2.8 Hz), 8.24 (d, 1H, J=2.8 Hz), 8.06 (d, 1H, J=7.6 Hz), 7.96 (d, 1H, J=7.6 Hz), 7.60-7.75 (m, 3H), 7.31 (dd, 1H, J=7.2, 1.2 Hz), 3.33 (q, 2H, J=7.2 Hz), 1.37 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C18H15N3O2S, 338; found 338.

Workup

concentrationconcentrated in vacuo
customPurification by silica gel chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-0f0f2d4286644bdd89f6776e312f058b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318939B2

Reaction notes

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