Water → HCID 59618693, compound

HRID 1691469Notes

Reaction equation

HRID 1691469 reaction equation
Br[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][N:7]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:6]=2[CH:33]=1.[CH3:34][N:35]1[CH:39]=[CH:38][C:37]([Sn](CCCC)(CCCC)CCCC)=[N:36]1.O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([S:20]([N:7]2[C:6]3[CH:33]=[C:2]([C:39]4[N:35]([CH3:34])[N:36]=[CH:37][CH:38]=4)[CH:3]=[CH:4][C:5]=3[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]2)(=[O:22])=[O:21])=[CH:28][CH:27]=1)([CH3:30])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 962WaterHCID 19028447204385-09-1HCID 596186368-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine2×

Product 1

HCID 59618693HCID 59618693, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 53, 100 mg, 0.185 mmol), 1-methyl-3-(tributylstannyl)-1H-pyrazole (62.4 mg, 0.168 mmol, prepared according to Heterocycles, 1997, 45, 1463), and PdCl2(PPh3)2 (11.8 mg, 0.0168 mmol) in THF (1.0 mL) was refluxed overnight. After cooling to room temperature, water was added, the reaction mixture was extracted with EtOAc, and the organic extracts were washed with water, brine, dried over MgSO4 and concentrated. The residue was purified via reverse phase HPLC to provide the title compound. LC/MS: m/e 542.1 (M+H)+. 1H NMR (500 MHz, CD3OD): δ 7.66 (1H, d), 7.59 (1H, s), 7.50 (1H, s), 7.38 (111, d), 7.18 (2H, d), 7.08-7.13 (2H, m), 6.97 (2H, d), 6.40 (1H, s), 4.60-5.00 (2H, br s), 3.97 (3H, s), 1.26 (9H, s).

Workup

  1. temperaturewas refluxed overnight
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washthe organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-408b6c84187f48f4b95902031f9349e7
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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