2-(Tributylstannyl)-1,3-thiazole → HCID 44554425, compound

HRID 1254064Notes

Reaction equation

HRID 1254064 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:11]([CH3:21])[C:12]=2[S:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:33]1[S:34][CH:35]=[CH:36][N:37]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][C:12]2[N:11]([CH3:21])[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([C:33]3[S:34][CH:35]=[CH:36][N:37]=3)=[CH:3][CH:4]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 44555246HCID 44555246, compound

Product 1

HCID 44554425HCID 44554425, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-{4-(4-bromophenyl)-5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-2-yl}pyridine (Example 15, 200 mg, 0.438 mmol), 2-(tributylstannyl)-1,3-thiazole (0.138 mL, 0.438 mmol), and tetrakis (50 mg, 0.044 mmol) was dissolved in toluene and heated at 150° C. for 20 min via microwave irradiation. The solvent was evaporated and the residue purified via column chromatography to afford the title compound. 1H NMR (500 MHz, (CD3)2CO): δ 8.71 (d, 1H), 8.40 (d, 1H), 8.40 (d, 2H), 8.32 (d, 2H), 8.00 (m, 1H), 7.90 (d, 1H), 7.63 (d, 1H), 7.46 (m, 1H), 7.36 (d, 2H), 7.20 (d, 2H), 4.18 (s, 3H). LCMS: m/z 461.0 (M+H)+. Human FAAH lysate assay: IC50=14.3 nM.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified via column chromatography

Sources & evidence

ORD record
ord-e20090366e404bf18684df67eed346d0
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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