Potassium Carbonate → (4-bromo-1H-indol-2-yl)(pyrrolidin-1-yl)methanone

HRID 1811018Notes

Reaction equation

HRID 1811018 reaction equation
[Br:1][C:2]1[C:3]([CH3:16])=[C:4]([NH:8][C:9]([C:11]2[NH:12][CH:13]=[CH:14]N=2)=O)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-:18].[K+].[K+].Br[CH2:24][CH:25](OCC)OCC>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:16]=[C:9]([C:11]([N:12]1[CH2:13][CH2:14][CH2:25][CH2:24]1)=[O:18])[NH:8]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 66606432N-(3-bromo-2-methylphenyl)-1H-imidazole-2-carboxamide

Product 1

HCID 59375103(4-bromo-1H-indol-2-yl)(pyrrolidin-1-yl)methanoneYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step 2 A solution of N-(3-bromo-2-methylphenyl)-1H-imidazole-2-carboxamide (0.70 g, 2.499 mmol) in DMF (12.5 mL) was treated with potassium carbonate (0.794 g, 5.75 mmol) and 2-bromo-1,1-diethoxyethane (0.395 mL, 2.62 and the mixture was stirred at rt. After 18.25 h, the mixture was diluted with EtOAc, filtered to remove some tan solid, and washed sequentially with 1 M hydrochloric acid and NaHCO3 (aq), and dried and concentrated to provide (4-bromo-1H-indol-2-yl)(pyrrolidin-1-yl)methanone as a tan solid (205 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ 11.96 (s, 1 H) 7.46 (d, J=7.9 Hz, 1 H) 7.27 (d, J=7.5 Hz, 1 H) 7.06-7.17 (m, 1 H) 6.82 (s, 1 H) 3.85 (t, J=6.8 Hz, 2 H) 3.55 (t, J=6.8 Hz, 2 H) 1.93-2.04 (m, 2 H) 1.81-1.92 (m, 2 H). Mass spectrum m/z 293, 295 (M+H)+.

Workup

  1. filtrationfiltered
  2. customto remove some tan solid
  3. washwashed sequentially with 1 M hydrochloric acid and NaHCO3 (aq)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3ae2122e3a44bfa97d84b28580753d2
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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