Pyridine → 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

HRID 1691430Notes

Reaction equation

HRID 1691430 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[N:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:9]=3[CH2:8][NH:7][C:6]=2[CH:20]=1.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[N:12]=[C:13]([C:16]([F:19])([F:17])[F:18])[CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([S:31]([C:28]3[CH:29]=[CH:30][C:25]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:26][CH:27]=3)(=[O:33])=[O:32])[C:6]=2[CH:20]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 669016538-bromo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine2×

Product 1

HCID 596186368-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 8-bromo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (5.16 g, 15 mmol, intermediate 36), (4-tert-butylphenyl)sulfonyl chloride (10.5 g, 45 mmol), pyridine (7.11 g, 90 mmol), DMAP (0.366 g, 3 mmol in DCM (75 mL) was stirred at rt for 24 h. The reaction was quenched with water, and the product was extracted with EtOAc (3×). The combined extracts were washed with water and brine, dried (MgSO4), filtered and concentrated. The residue was recrystallized from DCM and hexanes to afford the title compound. LC/MS: m/e 542.0 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.76 (1H, d, J=2.3 Hz), 7.56 (1H, d, J=7.3 Hz), 7.36 (1H, dd, J=8.7, 2.3 Hz), 7.11 (2H, d, J=8.5 Hz), 7.09 (1H, d, J=7.5 Hz), 6.96 (2H, d, J=8.4 Hz), 6.72 (1H, s), 6.62 (1H, d, J=8.7 Hz), 4.70-4.90 (2H, br), 1.25 (9H, s).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe product was extracted with EtOAc (3×)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from DCM and hexanes

Sources & evidence

ORD record
ord-079ee268058b4070a8c352e523291542
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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