Water → HCID 71599639, compound

HRID 1622452Notes

Reaction equation

HRID 1622452 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[NH:7][C:6]=2[CH:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:3]=1.Br[CH2:19][C:20]1[C:25]2[S:26][CH:27]=[CH:28][C:24]=2[CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[S:26]1[CH:27]=[CH:28][C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:19][N:7]3[C:6]4[CH:5]=[C:4]([N:12]5[CH2:17][CH2:16][O:15][CH2:14][CH2:13]5)[CH:3]=[C:2]([Br:1])[C:10]=4[N:9]=[C:8]3[CH3:11])[C:25]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 107517617-(Bromomethyl)-1-benzothiophene2×HCID 569605414-(4-bromo-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine

Product 1

HCID 71599639HCID 71599639, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To the mixture of 4-(4-bromo-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine (0.8 g, 2.70 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added 7-(bromomethyl)benzo[b]thiophene (0.920 g, 4.05 mmol)) and potassium carbonate (1.120 g, 8.10 mmol). The resulting reaction mixture was stirred at 90° C. for 2 h, then more 7-(bromomethyl)benzo[b]thiophene (0.920 g, 4.05 mmol) was added in and the reaction mixture was stirred at 100° C. for 4 h. It was cooled to room temperature and poured into water (100 mL). The aqueous mixture was extracted with DCM (100 mL×2). The combined organic phase was washed with Brine (100 mL) and concentrated. The crude material was purified on silica column (20˜90% EtOAc in Hexane) to give the product as solid (0.69 g, 58% %). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.42 (s, 3H) 2.95-3.07 (m, 4H) 3.66-3.72 (m, 4H) 5.69 (s, 2H) 6.81 (d, J=7.07 Hz, 1H) 7.00 (d, J=2.02 Hz, 1H) 7.09 (d, J=2.02 Hz, 1H) 7.36 (t, J=7.58 Hz, 1H) 7.53 (d, J=5.56 Hz, 1H) 7.79 (d, J=5.56 Hz, 1H) 7.85 (d, J=7.65 Hz, 1H); MS (ES+) m/e 442.0 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at 100° C. for 4 h
  3. temperatureIt was cooled to room temperature
  4. extractionThe aqueous mixture was extracted with DCM (100 mL×2)
  5. washThe combined organic phase was washed with Brine (100 mL)
  6. concentrationconcentrated
  7. customThe crude material was purified on silica column (20˜90% EtOAc in Hexane)

Sources & evidence

ORD record
ord-e24dad5369fa4ed9ac8566ad10ff5ad0
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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