Sodium Bicarbonate → HCID 10274902, compound

HRID 1744445Notes

Reaction equation

HRID 1744445 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][C:14](=N)[C:13]=2[C:27]#[N:28])[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].C([O-])(O)=[O:30].[Na+]>C1COCC1.O.[Cl-].[Cl-].[Zn+2]>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][C:14](=[O:30])[C:13]=2[C:27]#[N:28])[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 10113999HCID 10113999, compound

Product 1

HCID 10274902HCID 10274902, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-2-imino-7-methyl-2H-pyrrolo[2,3-h]chromene (100 mg, 0.216 mmol) in THF:water (10:2) was added a ZnCl2 solution (1 mL, 1.0 M in CH2Cl2). The solution was stirred at room temperature for approximately 7 h. The reaction mixture was made basic with saturated NaHCO3 (10 mL), and extracted with EtOAc (2×25 mL). The EtOAc extracts were washed with brine (10 mL), dried over MgSO4, and evaporated to yield a yellow solid. The solid was purified by flash column chromatography (silica gel, EtOAc:hexanes 30-70% EtOAc) to yield 17 mg (18%) of the product as a yellow solid. 1H NMR (acetone-d6): 7.51-7.48 (m, 2H), 7.42 (d, J=1.8 Hz, 1H), 7.34 (d, J=2.1 Hz, 1H), 7.17 (d, J=8.7 Hz, 1H), 6.91 (dd, J=0.6, 3.3 Hz, 2H), 3.98 (s, 3H), 3.97 (s, 3H), 3.85 (s, 3H).

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. washThe EtOAc extracts were washed with brine (10 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto yield a yellow solid
  6. customThe solid was purified by flash column chromatography (silica gel, EtOAc:hexanes 30-70% EtOAc)

Sources & evidence

ORD record
ord-a702597d138145baa4b1d3ce850b1a49
Source dataset
uspto-grants-2006_03
Patent number
US07015328B2

Reaction notes

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