Potassium Carbonate → ethyl 7-(4-methylbenzoyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854881Notes

Reaction equation

I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.[C:31]([O-])([O-])=[O:32].[K+].[K+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([C:31]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]3)=[CH:4][CH:3]=2)=[O:32])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The ethyl 7-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 9a, Step 2 (3.0 g, 7.53 mmol), 4-methylphenylboronic acid (1.11 g, 8.26 mmol), K2CO3 (3.12 g, 22.59 mmol), and PdCl2(PPh3)2 (159 mg, 0.225 mmol) were mixed in dioxane (30 mL) in a sterling bomb. Carbon monoxide was bubbling to 40 psi. The reaction was heated to 80° C. for 5 h. After filtration, the reaction was quenched with NH4Cl and extracted with EtOAc. The organic layer was washed and dried over MgSO4. The filtrate was evaporated and dried in vacuo to afford yellow solid (1.2 g, 41%): LCMS m/z 391.10 (M+H). 1H NMR (CDCl3/400 MHz) 7.75 (s, 1H), 7.69 (d, 2H, J=8.0 Hz), 7.39(d, 1H, J=8.0 Hz), 7.36 (s, 1H), 7.31 (d, 1H, J=8.0 Hz), 7.28 (d, 2H, J=8.0 Hz), 7.25(s, 1H), 5.78 (q, 1H, J=6 Hz), 4.33 (m, 2H), 2.43(s, 3H), 1.35 (t, 3H, J=7.2 Hz).

Workup

customCarbon monoxide was bubbling to 40 psi
filtrationAfter filtration
customthe reaction was quenched with NH4Cl
extractionextracted with EtOAc
washThe organic layer was washed
dry with materialdried over MgSO4
customThe filtrate was evaporated
customdried in vacuo

Sources & evidence

ORD record: ord-41b47c393ed0424b8ee4174a46d383a8
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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