Cesium carbonate → HCID 86658552, compound

HRID 1520197Notes

Reaction equation

HRID 1520197 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH2:19])[S:16][C:17]=3[CH3:18])[CH:10]=[N:9]2)=[CH:5][CH:4]=1.Cl[C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][N:24]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:23]4[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][N:24]=4)[S:16][C:17]=3[CH3:18])[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27827922-Chloro-4-fluoropyridineHCID 86658553HCID 86658553, compound

Product 1

HCID 86658552HCID 86658552, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

According to Scheme 3 Step 2: A solution of 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methylthiazol-2-amine (0.47 mmol, 140 mg), 2-chloro-4-fluoropyridine (0.47 mmol, 61 mg), Xantphos (70 μmol, 40.5 mg), Pd(OAc)2 (46 μmol, 10.5 mg) and cesium carbonate (0.93 mmol, 304 mg) in dioxane (6.5 mL) was microwaved at 135° C. for 2 hours under nitrogen. After evaporation of the solvent, the resulting crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (80:20) as eluent to afford N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methylthiazol-2-yl)-4-fluoropyridin-2-amine (0.33 mmol, 132 mg, 71%).

Workup

  1. customAfter evaporation of the solvent
  2. customthe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-570d37683d1e419ebd5a71590e37e3a2
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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