Sodium Carbonate → 8-Chloro-2-(pyridin-3-yl)quinoline-3-carbaldehyde

HRID 572118Notes

Reaction equation

Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1>COCCOC.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>[Cl:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:23]1[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=1)[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2,8-dichloroquinoline-3-carbaldehyde (5.0 g, 22.2 mmol), Na2CO3 (3.51 g, 33.2 mmol) and 3-pyridylboronic acid (2.72 g, 22.2 mmol) in DME (60 mL) and water (30 mL) was degassed by bubbling N2 through it for 5 minutes. Pd(PPh3)4 (1.28 g, 1.11 mmol) was added and the mixture heated at 90° C. for 7 h. The mixture was allowed to cool to room temperature. The resultant precipitate was filtered off and washed with water (5×50 mL) and diethyl ether (5×50 mL) to give the title compound (5.4 g, 91%) as a tan solid. δH (DMSO-d6) 10.15 (s, 1H), 9.15 (s, 1H), 8.94 (dd, J 2.3, 0.8 Hz, 1H), 8.77 (dd, J 4.9, 1.7 Hz, 1H), 8.31 (dd, J 8.3, 1.3 Hz, 1H), 8.20-8.19 (m, 1H), 8.18-8.16 (m, 1H), 7.75 (dd, J 7.9, 7.5 Hz, 1H), 7.62 (ddd, J 7.7, 4.9, 0.8 Hz, 1H). LCMS (ES+) 269 (M+H)+, RT 1.82 minutes.

Workup

customwas degassed
customby bubbling N2 through it for 5 minutes
temperatureto cool to room temperature
filtrationThe resultant precipitate was filtered off
washwashed with water (5×50 mL) and diethyl ether (5×50 mL)

Sources & evidence

ORD record: ord-c9d03e2476814f25b4ab5997e35ae34a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029392B2

Reaction notes

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