Sodium Bicarbonate → (3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)(morpholino)methanone

HRID 729797Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine(3 g, 15 mmol), 3-(morpholine-4-carbonyl)phenylboronic acid (4 g, 18 mmol), sodium bicarbonate (4 g, 46 mmol), and tetrakis(triphenylphosphine)palladium(0) in dioxane/water (100 mL/20 mL) was stirred at 110° C. for 15 hours. The mixture was then poured into ice water and extracted with ethyl acetate (3×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to dryness. Silica gel chromatography of the crude product afforded (3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)(morpholino)methanone (3.86 g, 84% yield) as yellow solids. MS: m/z 308.1 (M+H+).

Workup

extractionextracted with ethyl acetate (3×)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-8088b661ca6648149508a8762c7732f1
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582637B2

Reaction notes

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