Water → HCID 57500672, compound

HRID 2420966Notes

Reaction equation

Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9]C)=O.Cl.N[C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])(=O)C.[Na+].O.C[N:33](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:3]2[N:4]=[CH:5][S:6][C:2]=2[C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:14]=2[NH:33]1

Participants

Conditions

Temperature: 120 °C

Procedure

In a microwave vessel, methyl 5-bromothiazole-4-carboxylate (1.0 eq, 97 mg, 0.44 mmol), 2-amino-3-methoxycarbonyl phenyl boronic acid HCl (1.1 eq, 111 mg, 0.48 mmol), sodium acetate (3.0 eq, 107 mg, 1.31 mmol) and PdCl2(dppf) (0.05 eq, 11 mg, 0.022 mmol) were mixed together in anhydrous DMF (1 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 combined extracts were washed with brine, dried over Na2SO4 and the solvents removed by evaporation. The material was dissolved in a mixture of CH2Cl2 and MeOH and the solution filtered through a pad of celite. Evaporation of the volatiles afforded crude methyl 4-oxo-4,5-dihydrothiazolo[4,5-c]quinoline-7-carboxylate as a black solid (44 mg, 39% yield). A small part of the compound was subjected to preparative HPLC for analytical purpose. LCMS (ES): 95% pure, m/z 261 [M+1]+.

Workup

extractionthe material extracted with CH2Cl2
washThe combined extracts were washed with brine
dry with materialdried over Na2SO4
customthe solvents removed by evaporation
dissolutionThe material was dissolved in a mixture of CH2Cl2 and MeOH
filtrationthe solution filtered through a pad of celite
customEvaporation of the volatiles

Sources & evidence

ORD record: ord-ae6f3a60a1aa40ee87dc7d45a0f15bff
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956064B2

Reaction notes

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