Potassium Carbonate → HCID 86636435, compound

HRID 1483686Notes

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[N:3]=1.[Br:16][C:17]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:18]=1[CH:19]=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:16][C:17]1[CH:24]=[CH:23][C:22]([O:25][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[N:3]=2)=[CH:21][C:18]=1[CH:19]=[O:20]

Participants

Conditions

Temperature: 69 °C

Procedure

To a mixture of 6-chloro-2-cyclopentyloxy-nicotinonitrile (1.32 g, 5.92 mmol) and 2-bromo-5-hydroxy-benzaldehyde (1.43 g, 7.10 mmol) in DMF (10 mL) was added potassium carbonate (1.22 g, 8.88 mmol). The resulting mixture was heated at 69° C. overnight. DMF was removed under reduced pressure, the residue was diluted with EtOAc (100 mL), washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to give white solid, which was purified by flash chromatography on silica gel using 10-25% EtOAc/hexanes as eluent to yield the title compound (2.30 g, quantitative) as white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.19 (s, 1H), 8.24 (d, J=8.2 Hz, 1H), 7.88 (d, J=8.6 Hz, 1H), 7.70 (s, 1H), 7.60-7.46 (m, 1H), 6.79 (d, J=8.2 Hz, 1H), 4.95 (br. s., 1H), 1.87-1.50 (m, 6H), 1.52-1.30 (m, 2H).

Workup

customDMF was removed under reduced pressure
additionthe residue was diluted with EtOAc (100 mL)
washwashed with water (30 mL) and brine (30 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give white solid, which
customwas purified by flash chromatography on silica gel using 10-25% EtOAc/hexanes as eluent

Sources & evidence

ORD record: ord-8c45edc8e031451da0ab265fe7608b91
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416146B2

Reaction notes

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