Dichloromethane → HCID 59238889, compound

HRID 1949117Notes

Reaction equation

HRID 1949117 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9]([O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[C:8]3[NH:21][C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][C:27]=4[C:7]3=[CH:6][C:5]2=1.[Br:29]Br.C(Cl)Cl>CN(C=O)C>[Br:29][C:6]1[C:7]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=3)[NH:21][C:8]=2[C:9]([O:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])=[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][C:2]([F:1])=[CH:3][C:4]=3[C:5]=12

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 45138929HCID 45138929, compound

Product 1

HCID 59238889HCID 59238889, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-dimethylethanamine (213.9 mg, 0.5638 mmol) in DMF (20 mL) at 0° C. was added Br2 in CH2Cl2 (50 mg/mL, 1.982 mL, 0.6201 mmol). The reaction was warmed to room temperature and stirred for two hours. DMF was removed via vacuum pump. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aq. NaCO3. The organic layers was concentrated and subjected to flash chromatography to provide the title compound (188.4 mg, 73%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.89 (br s, 2 H), 8.39 (dd, J=10.0, 2.4 Hz, 2 H), 7.55 (dd, J=8.8, 4.4 Hz, 2 H), 7.31 (td, J=8.8, 2.4 Hz, 2 H), 4.34 (t, J=5.2 Hz, 2 H), 2.74 (t, J=5.6 Hz, 2 H), 2.36 (s, 6 H); MS (ESI) m/z 456.1 (M−H)−; MS (ESI) m/z 458.0 (M+H)+

Workup

  1. customDMF was removed via vacuum pump
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with saturated aq. NaCO3
  4. concentrationThe organic layers was concentrated

Sources & evidence

ORD record
ord-2db37d0b91ff4ad2bbf3f8e9a9522211
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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