Sodium Carbonate → 3-(2-tert-butoxy-6-phenylpyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 68340Notes

Reaction equation

[C:1]([O:5][C:6]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[C:8](Cl)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].C(COC)OC.C(O)C.O.[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[C:8]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of EXAMPLE 34C (0.13 g, 0.43 mmol) in 7:3:2 dimethoxyethane/ethanol/water (3 mL) was added phenyl boronic acid (0.053 g, 0.43 mmol), 1M aqueous sodium carbonate (0.6 mL) and dichlorobis (triphenylphosphine)-palladium (II) (0.015 g, 0.022 mmol). The solution was heated to 160° C. in a CEM microwave @100 W for 20 minutes. The crude material was diluted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography (Analogix 280, gradient elution, 5-75% ethyl acetate/hexane) gave the title compound. MS (ESI) m/e 344.0 (M+H)+.

Workup

customfor 20 minutes
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customPurification
washby flash chromatography (Analogix 280, gradient elution, 5-75% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-1ba44848956d444286b05d8a93b2232f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822446B2

Reaction notes

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