Sodium Carbonate → HCID 66753265, compound

HRID 1642392Notes

Reaction equation

HRID 1642392 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11](C#N)=[CH:10][CH:9]=1.[F:20][C:21]([F:33])([F:32])[O:22]C1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].FC1C=C(C2C(=O)N3C=CSC3=NC=2C)C=C(F)C=1>C1(C)C=CC=CC=1.O.C(O)C>[CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([O:22][C:21]([F:33])([F:32])[F:20])=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 66752927HCID 66752927, compoundHCID 667534716-(3,5-Difluorophenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 66753265HCID 66753265, compoundYield 68.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The title compound was prepared by coupling reaction of Step 2 of Intermediate 4 (9.5 g, 37.312 mmol) with 4-(trifluoromethoxy)phenyl boronic acid (9.5 g, 32.523 mmol) in the presence of Pd[(C6H5)3P]4 (1.5 g, 1.301 mmol) and sodium carbonate (20.6 g, 195.13 mol) in a mixture of toluene, ethanol and water according to the procedure described in Intermediate 3, step 3 yielded 7.3 g of the desired compound as a pale yellow solid; IR (KBr) 3088, 1658, 1646, 1513, 1269, 1160 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 2.18 (s, 3H), 7.42-7.4 (m, 4H), 7.53 (d, J=4.8 Hz, 1H), 8.01 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 327.16 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c02a91f58a8840b1acd0c24d396a56e4
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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