Dichloromethane → HCID 10180948, compound

HRID 1768431Notes

Reaction equation

HRID 1768431 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-01a430860a5c4355bc3683388ee4f1ab
Source dataset
uspto-grants-2007_06
Patent number
US07235674B2

Reaction notes

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