Potassium Carbonate → HCID 135985748, compound

HRID 2264790Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][CH:3]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C.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>[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of ethyl 6-bromo-2-pyridinecarboxylate (D1, 460 mg, 2.0 mmol) in dioxane (4 ml) were added 4-hydroxy-phenyl boronic acid (414 mg, 3.0 mmol), Pd(PPh3)4 (450 mg, 0.4 mmol) and potassium carbonate (420 mg, 4.0 mmol) dissolved in water (2 ml). The reaction mixture was heated in a microwave synthesizer for 15 min at 150° C. The reaction mixture was diluted with ethyl acetate (150 ml) and washed with saturated aqueous ammonium chloride (40 ml). The resulting crude material was purified by chromatography on silica gel using ethyl acetate/cyclohexanes (1:1) to afford the title compound (340 mg, 72%); 1H-NMR (300 MHz, CDCl3) δ (ppm): 8.05 (d, 2H), 8.0 (m, 1H), 7.80 (d, 2H), 7.05 (d, 2H), 6.80 (bt, 1H), 4.50 (q, 2H), 1.45 (t, 3H).

Workup

washwashed with saturated aqueous ammonium chloride (40 ml)
customThe resulting crude material was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-7c38bc59b84f46b39b7f74c73bc7dd0a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855218B2

Reaction notes

Loading…