Phenylboronic Acid → HCID 86658567, compound

HRID 1520215Notes

Reaction equation

HRID 1520215 reaction equation
Br[C:2]1[C:6]([C:7]2[N:8]=[C:9]([NH:12][C:13]3[N:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=3)[S:10][CH:11]=2)=[CH:5][N:4]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:3]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.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>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:4]2[CH:5]=[C:6]([C:7]3[N:8]=[C:9]([NH:12][C:13]4[N:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=4)[S:10][CH:11]=3)[C:2]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:3]2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 86658568HCID 86658568, compound

Product 1

HCID 86658567HCID 86658567, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

According to Scheme 12 Step 1: A solution of 4-(3-bromo-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-N-(4-methylpyrimidin-2-yl)thiazol-2-amine (0.33 mmol, 150 mg), phenylboronic acid (0.39 mmol, 48 mg), Pd(PPh3)4 (49 μmol, 57 mg) and a saturated aqueous solution of NaHCO3 (0.5 mL) in dioxane (0.5 mL) was stirred at 120° C. for 2 hours under microwave heating. The crude mixture was filtered through celite pad and washed with DCM. The filtrate was washed with water. The organic layer was dried over MgSO4, was filtered and was concentrated. The crude compound was purified by flash chromatography with silica gel using DCM/AcOEt (100:0 to 70:30) to yield 4-(1-(4-methoxybenzyl)-3-phenyl-1H-pyrazol-4-yl)-N-(4-methylpyrimidin-2-yl)thiazol-2-amine (0.17 mmol, 77 mg, 52%).

Workup

  1. temperatureheating
  2. filtrationThe crude mixture was filtered through celite pad
  3. washwashed with DCM
  4. washThe filtrate was washed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationwas filtered
  7. concentrationwas concentrated
  8. customThe crude compound was purified by flash chromatography with silica gel

Sources & evidence

ORD record
ord-068537fdfd9644ba972fb2c223186ce3
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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