Water → HCID 50941660, compound

HRID 1919644Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.Cl.N[C:13]1[C:18]([C:19]#[N:20])=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])(=O)C.[Na+].O.C[N:31](C=O)C>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]>[O:9]=[C:7]1[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[C:15]2[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:13][C:14]=2[NH:31]1

Participants

Conditions

Temperature: 120 °C

Procedure

In a microwave vessel, methyl 2-bromo-3-thiophene carboxylate (1.0 eq, 250 mg, 1.13 mmol), 2-amino-3-cyanophenyl boronic acid HCl (1.1 eq, 250 mg, 1.24 mmol), sodium acetate (3.0 eq, 278 mg, 3.39 mmol) and PdCl2(dppf) (0.007 eq, 4.3 mg, 0.0082 mmol) were mixed together in anhydrous DMF (2.5 ml). The mixture was heated in a microwave oven at 120° C. for 10 nm. Water was added and the material extracted with CH2Cl2. The organic extracts were washed with brine, dried over Na2SO4 and the solvents removed in vacuo. The resulting solid was sonicated in AcOEt, filtered and dried to afford 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carbonitrile as a beige solid (121 mg, 48% yield). LCMS (ES): 95% pure, m/z 227 [M+1]+.

Workup

extractionthe material extracted with CH2Cl2
washThe organic extracts were washed with brine
dry with materialdried over Na2SO4
customthe solvents removed in vacuo
customThe resulting solid was sonicated in AcOEt
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-8c5e1b51b7d24850928c87653fbb6e79
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168651B2

Reaction notes

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