Ethanol → HCID 66753116, compound

HRID 1642380Notes

Reaction equation

HRID 1642380 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C.FC1C=C([C:31]2[C:36](=[O:37])[N:35]3[CH:38]=[CH:39][S:40][C:34]3=[N:33][C:32]=2[CH3:41])C=C(F)C=1>C1(C)C=CC=CC=1.CC1N=C2SC=CN2C(=O)C=1C1C=CC(C#N)=CC=1.O>[CH3:41][C:32]1[N:33]=[C:34]2[S:40][CH:39]=[CH:38][N:35]2[C:36](=[O:37])[C:31]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 667534716-(3,5-Difluorophenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 66753116HCID 66753116, compound

Reagents, catalysts & solvents 3

HCID 66752927HCID 66752927, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The title compound was prepared by coupling reaction of Step 2 intermediate from Intermediate 4 (600 mg, 2.001 mmol) with 3-(trifluoromethyl)phenyl boronic acid (585 g, 3.020 mmol) in the presence of Pd[(C6H5)3P]4 (92 mg, 0.0812 mmol) and sodium carbonate (1.27 g, 12.061 mol) in a mixture of toluene, ethanol and water according to the procedure described in Intermediate 3, step 3 1.21 g yielded 18.5 g of the desired compound as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 2.18 (s, 3H), 7.53-7.59 (m, 4H), 7.58-7.80 (m, 1H), 8.01 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 311.28 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-95ffdbaeb2714f8985abd56a3a60dcb0
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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