Ethanol → HCID 66753266, compound

HRID 1642409Notes

Reaction equation

HRID 1642409 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[O:19])[C:10]=1C1C=CC(C#N)=CC=1)[C:7]1[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=1[S:5]2.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=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:29]1[CH:30]=[CH:31][C:26]([C:25]([F:36])([F:35])[F:24])=[CH:27][CH:28]=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 27343894-(Trifluoromethyl)phenylboronic acidHCID 667526544-(2-Methyl-4-oxo-4H-pyrimido[2,1-b][1,3]benzothiazol-3-yl)benzonitrile

Product 1

HCID 66753266HCID 66753266, compoundYield 107.8%

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-trifluoromethylphenylboronic acid (1.50 g, 8.18 mmol) in the presence of Pd[(C6H5)3P]4 (270 mg, 0.233 mmol) and sodium carbonate (3.71 g, 35.07 mmol) in a mixture of toluene, ethanol and water to afford 2.27 g of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 2.30 (s, 3H), 7.42-7.48 (m, 2H), 7.65-7.67 (m, 2H), 8.00-8.03 (m, 2H), 8.86-8.88 (m, 2H); ESI-MS (m/z) 361.32 (M+H)+.

Sources & evidence

ORD record
ord-bcd107232b5a426dbaa90f834bb062f2
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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