Sodium Carbonate → HCID 66753238, compound

HRID 1642413Notes

Reaction equation

HRID 1642413 reaction equation
I[C:2]1[C:10](=[O:11])[N:9]2[C:5]([N:6]([CH3:16])[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=32)=[N:4][C:3]=1[CH3:17].[F:18][C:19]([F:31])([F:30])[O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=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>[CH3:17][C:3]1[N:4]=[C:5]2[N:9]([C:10](=[O:11])[C:2]=1[C:24]1[CH:23]=[CH:22][C:21]([O:20][C:19]([F:18])([F:30])[F:31])=[CH:26][CH:25]=1)[C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=1[N:6]2[CH3:16]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 66753013HCID 66753013, compoundHCID 667534716-(3,5-Difluorophenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 66753238HCID 66753238, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of Step 3 intermediate (1.2 g, 3.512 mmol), 4-trifluoromethoxyphenyl boronic acid (0.864 g, 4.212 mmol), Pd[(C6H5)3P]4 (0.161 g, 1.420 mmol), Na2CO3 (2.32 g) was reacted together in a mixture of toluene (20 ml), ethanol (5 ml) and water (5 ml) according to the procedure outlined in Step 3, Intermediate 3 to afford the desired compound: 1H NMR (300 MHz, DMSO-d6) δ 2.24 (s, 3H), 3.78 (s, 3H), 7.33-7.46 (m, 4H), 7.52-7.57 (m, 1H), 7.68-7.71 (m, 1H), 8.40-8.43 (s, 1H); ESI-MS (m/z) 374.62 (M+H)+.

Sources & evidence

ORD record
ord-89f6c52522ba4cdba06f988b234a5ebd
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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