Cesium carbonate → HCID 118699712, compound

HRID 1773318Notes

Reaction equation

[S:1]1[C:13]2[C:12]3[CH2:11][CH2:10][NH:9][CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[CH:3]=[CH:2]1.[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19](Br)[CH:18]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:19]4[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=4)[C:16]([O:15][CH3:14])=[O:24])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6,7,8,9-Tetrahydrothieno[3,2-c]-2,7-naphthyridine (3.0 g, 15.77 mmol, prepared as previously described), methyl-3-bromobenzoate (3.90 g, 18.14 mmol), palladium(II)acetate (354 mg, 1.577 mmol), racemic BINAP (982 mg, 1.577 mmol) and cesium carbonate (7.19 g, 22.08 mmol) in toluene (270 ml) was heated at 100° C. with stirring for 18 hours. Upon cooling to room temperature, the insolubles were filtered off (celite) and washed with EtOAc. The washing was combined with the filtrate and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, EtOAc) gave the product as a yellow glass (3.54 g, 69%). MS (APCl): (M+1)+=325;

Workup

customprepared
temperatureUpon cooling to room temperature
filtrationthe insolubles were filtered off (celite)
washwashed with EtOAc
concentrationconcentrated
washElution through a flash column (silica gel 60, 230-400 mesh, EtOAc)

Sources & evidence

ORD record: ord-1aaaef26583f4ea6b9fcb5f9abee7d42
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255096B1

Reaction notes

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