Sodium Bicarbonate → HCID 69002937, compound

HRID 1821351Notes

Reaction equation

HRID 1821351 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[C:3]=1[OH:19].[CH3:20][N:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](Cl)=O.C(=O)([O-])O.[Na+]>O1CCOCC1>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](/[CH:9]=[CH:8]/[C:4]2[C:3]3[O:19][C:26]([C:22]4[N:21]([CH3:20])[CH:25]=[CH:24][CH:23]=4)=[N:1][C:2]=3[CH:7]=[CH:6][CH:5]=2)=[N:11]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27950921-Methyl-1H-pyrrole-2-carbonyl chlorideHCID 136381714HCID 136381714, compound

Product 1

HCID 69002937HCID 69002937, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
210 °C

Procedure

A solution of (E)-2-amino-6-[2-(1H-indazol-3-yl)vinyl]phenol (0.10 g, 0.40 mmol) obtained in Step 2 in 1,4-dioxane (1.5 mL) was added with 1-methyl-1H-pyrrole-2-carbonyl chloride (63 mg, 0.44 mmol) and stirred at 210° C. for 15 minutes under microwave irradiation. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10) and crystallized from ethanol to obtain Compound 148 (13 mg, 10%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10)
  4. customcrystallized from ethanol

Sources & evidence

ORD record
ord-b7813b6e26334ecc9c0bb5bf6ef21f37
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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