Ethanol → 2-Methyl-3-[4-(trifluoromethoxy)phenyl]-4H-pyrimido[2,1-b][1,3]benzo thiazol-4-one

HRID 1642410Notes

Reaction equation

HRID 1642410 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[O:19])[C:10]=1[C:11]1[CH:18]=[CH:17][C:14](C#N)=[CH:13][CH:12]=1)[C:7]1[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=1[S:5]2.[F:24][C:25]([F:37])([F:36])[O:26]C1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[O:19])[C:10]=1[C:11]1[CH:18]=[CH:17][C:14]([O:26][C:25]([F:37])([F:36])[F:24])=[CH:13][CH:12]=1)[C:7]1[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=1[S:5]2

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 667526544-(2-Methyl-4-oxo-4H-pyrimido[2,1-b][1,3]benzothiazol-3-yl)benzonitrile

Product 1

HCID 667536762-Methyl-3-[4-(trifluoromethoxy)phenyl]-4H-pyrimido[2,1-b][1,3]benzo thiazol-4-oneYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The title compound was prepared by treatment of Step 2 intermediate, Intermediate 22 (2.0 g, 5.845 mmol) with 4-trifluoromethoxyphenylboronic acid (1.684 g, 8.183 mmol) in the presence of Pd[(C6H5)3P]4 (270 mg, 0.233 mmol) and sodium carbonate (3.11 g, 35.07 mmol) in a mixture of toluene, ethanol and water to afford 1.5 g of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 2.02 (s, 3H), 7.41-7.59 (m, 3H), 7.53-7.56 (m, 3H), 8.03-8.07 (m, 1H), 8.84-8.87 (m, 1H); ESI-MS (m/z) 377.17 (M+H)+.

Sources & evidence

ORD record
ord-03a4911837324993bd443c073adef635
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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