Pyridine → 6-(4-Bromo-phenyl)-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one

HRID 2384942Notes

Reaction equation

HRID 2384942 reaction equation
N1C=CC=CC=1.C(N(CC)CC)C.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:30][C:24]3[C:25](=[O:29])[NH:26][CH:27]=[CH:28][C:23]=3[CH:22]=2)=[CH:17][CH:16]=1.[Br:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>ClCCl>[Br:31][C:32]1[CH:37]=[CH:36][C:35]([N:26]2[CH:27]=[CH:28][C:23]3[CH:22]=[C:21]([C:18]4[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=4)[S:30][C:24]=3[C:25]2=[O:29])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 79599(4-Bromophenyl)boronic acidHCID 576495192-(4-Chlorophenyl)-6H,7H-thieno[2,3-c]pyridin-7-one

Product 1

HCID 689531476-(4-Bromo-phenyl)-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-oneYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add pyridine (0.62 mL, 7.64 mmol) and triethylamine (0.53 mL, 3.82 mmol) to a mixture of 2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (0.5 g, 1.91 mmol), 4-bromobenzeneboronic acid (1.15 g, 5.73 mmol), cupric acetate (1.05 g, 5.73 mmol), and 4A molecular sieves (0.4 g) in dichloromethane (38 mL). Stir the mixture at RT for 2 days. Dilute the mixture with CH2Cl2, wash twice with a solution of 5% NH4OH/H2O, and H2O. Dry the organics over Na2SO4, filter, wash with Et2O, and concentrate. Purify the crude material by flash chromatography eluting with 10-15% EtOAc/CH2Cl2 to give 0.2 g (25%) of the title compound. LC-ES/MS m/z (81Br, 35Cl) 417.8 [M+H]+.

Workup

  1. washwash twice with a solution of 5% NH4OH/H2O, and H2O
  2. dry with materialDry the organics over Na2SO4
  3. filtrationfilter
  4. washwash with Et2O
  5. concentrationconcentrate
  6. customPurify the crude material by flash chromatography
  7. washeluting with 10-15% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-fd022d2ac56e4943b9abbe4bf6c5cc11
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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