Sodium Carbonate → Methyl 3-fluoro-4-(6-methoxyquinolin-2-yl)benzoate

HRID 55829Notes

Reaction equation

N1C(C2C=CC([C:12]3[C:21](C)=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[CH:18]=4)[N:13]=3)=CC=2)=NN=N1.[F:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=1B1OC(C)(C)C(C)(C)O1)[C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[CH:18]=2)[N:13]=1)[C:29]([O:31][CH3:32])=[O:30]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-chloro-6-methoxyquinoline (Intermediate 1) (300 mg, 1.55 mmol), methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Intermediate 10) (415 mg, 1.48 mmol), Pd(dppf)Cl2 (110 mg, 0.15 mmol) and sodium carbonate (320 mg, 3.0 mmol) in 1,4-dioxane/water (6 mL/1 mL) was heated to 120° C. under microwave irradiation for 4 h. The precipitate was filtered and washed with EA. The combined filtrate was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EA=30/1) to give the product (220 mg, 46%) as white solid. MS (ESI): m/z 312.2 [M+1]+.

Workup

filtrationThe precipitate was filtered
washwashed with EA
washThe combined filtrate was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (PE/EA=30/1)

Sources & evidence

ORD record: ord-b44da6d7dba848138c8f9ad2e218b438
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09433618B2

Reaction notes

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