Pyrrolidine → HCID 58913103, compound

HRID 1296689Notes

Reaction equation

HRID 1296689 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:32]=[CH:31][C:8]([CH2:9][C:10]2[C:19]3[C:14](=[C:15]([I:21])[C:16]([OH:20])=[CH:17][CH:18]=3)[O:13][C:12](=[O:22])[C:11]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[CH:7][CH:6]=1.[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>C1COCC1>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[C:11]1[C:12](=[O:22])[O:13][C:14]2[C:19]([C:10]=1[CH2:9][C:8]1[CH:31]=[CH:32][C:5]([O:4][CH2:3][CH2:2][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:6][CH:7]=1)=[CH:18][CH:17]=[C:16]([OH:20])[C:15]=2[I:21]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 58913141HCID 58913141, compound

Product 1

HCID 58913103HCID 58913103, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred suspension 4-(4-(2-Bromoethoxy)-benzyl)-3-(2,4-dichlorophenyl)-7-hydroxy-8-iodo-chromen-2-one (1.90 g, 2.94 mmol) in anhydrous THF (20 mL) was added pyrrolidine (1.46 mL, 17.6 mmol), and the resulting yellow solution was heated at 85° C. for 1.5 h. The resultant mixture was cooled to room temperature and the solvent was removed in vacuo. The resultant residue was dissolved in CH2Cl2, washed with H2O and brine and dried (MgSO4). The organic phase was concentrated in vacuo. The resultant residue was purified using flash chromatography (200 g silica gel, 12:1→9:1→85:15 CH2Cl2:MeOH) to afford the title compound as a yellow solid (1.87 g, 100%). 1H NMR (300 MHz, CDCl3) δ 7.50 (d, J=2.0 Hz, 1H), 7.32 (d, J=8.8 Hz, 1H), 7.26 (dd, J=2.0, 8.0 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 6.95–6.86 (m, 3H), 6.77–6.70 (m, 2H), 4.30 (t, J=5.0 Hz, 2H), 4.00 (d, J=15.5 Hz, 1H), 3.76 (d, J=15.5 Hz, 1H), 3.25 (t, J=5.0 Hz, 2H), 3.19–3.04 (m, 4H), 2.04–1.91 (m, 4H); MS (ESI) m/z 635.6 (M)+; HPLC tR 5.85 min.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe resultant residue was dissolved in CH2Cl2
  3. washwashed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationThe organic phase was concentrated in vacuo
  6. customThe resultant residue was purified

Sources & evidence

ORD record
ord-b30f58b9939c4c45aa37d83f737a9e0a
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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