Dichloromethane → HCID 10180948, compound

HRID 1744454Notes

Reaction equation

HRID 1744454 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[CH:6][CH:5]=2.ClC1C(=O)C([C:36]#[N:37])=C(C#N)C(=O)C=1Cl.Cl[CH2:40]Cl>C(OCC)(=O)C>[NH:1]=[C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=2)[C:9]2[C:4](=[CH:5][C:6]([N:37]([CH3:36])[CH3:40])=[CH:7][CH:8]=2)[O:3]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10200202HCID 10200202, compound

Product 1

HCID 10180948HCID 10180948, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4 Å Molecular sieves (20 mg) were added to 2-amino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene (20 mg, 0.05 mmol) in dichloromethane (1 mL). The solution was stirred for approximately 15 min. Then 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (10 mg, 0.05 mmol, 1 eq.) was added and stirred continuously at room temperature for approximately 1 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with saturated aqueous sodium bicarbonate solution (20 mL) and brine (20 mL), and dried over sodium sulfate and concentrated to yield 17 mg (79%) of the desired compound. 1H NMR (DMSO-d6): 8.33 (s, 1H), 7.28 (d, J=1.9 Hz, 1H), 7.21 (d, J=1.9 Hz, 1H), 6.87 (d, J=9.1 Hz, 1H), 6.56 (dd, J=2.5, 9.1 Hz, 1H), 6.40 (d, J=2.5 Hz, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.03 (s, 6H).

Workup

  1. stirringstirred continuously at room temperature for approximately 1 h
  2. washwashed with saturated aqueous sodium bicarbonate solution (20 mL) and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e14f1a7e92d8435cb2baa3471e58444e
Source dataset
uspto-grants-2006_03
Patent number
US07015328B2

Reaction notes

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