Sodium Carbonate → N-[3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl]prop-2-enamide

HRID 1500824Notes

Reaction equation

[C:1](NC1C=C(B(O)O)C=CC=1)(=O)C=C.C(=O)([O-])[O-].[Na+].[Na+].[CH3:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[C:28]([C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=3)[CH:29]=2)[NH:24]N=1>C(O)C.C(Cl)Cl>[CH3:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[C:28]([C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=3)[CH:29]=2)[NH:24][CH:1]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 19 (50 mg, 0.2369 mmol) and 2 (50 mg, 0.2369 mmol) in ethanol and toluene (1:4 mL) was added sodium carbonate (49.74 mg, 0.4738 mmol). The reaction was degassed and purged with nitrogen for 15 min. Pd(dppf)Cl2.DCM (9.06 mg, 0.0114 mmol), and again degassed for 15 min. The reaction mixture was stirred for 2 h at 90° C. and the reaction mixture allowed to cool to rt and diluted with DCM (25 mL). The organic layer was filtered through Celite and concentrated to get the crude. The resulting oil was purified via silica gel chromatography using a gradient of 30% ethyl acetate:hexane to afford Compound 20. MS-ES+277 1H NMR (400 MHz, DMSO-D6) 20: 11.37 (d, 1H), 10.24 (d, 1H), 8.45 (d, 1H), 8.09 (d, 2H), 7.68 (d, 1H), 7.43 (d, 2H), 7.28 (d, 1H), 6.46 (d, 1H), 6.44 (d, 1H), 5.79 (d, 1H), 2.30 (d, 1H).

Workup

customThe reaction was degassed
custompurged with nitrogen for 15 min
temperatureto cool to rt
filtrationThe organic layer was filtered through Celite
concentrationconcentrated
customto get the crude
customThe resulting oil was purified via silica gel chromatography

Sources & evidence

ORD record: ord-f3d918c6ae28492aba217855d6b9c3a3
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206188B2

Reaction notes

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