Pyrazole → HCID 91086029, compound

HRID 1673249Notes

Reaction equation

HRID 1673249 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[O:14][C:15]([CH3:27])([CH3:26])[CH2:16][CH:17]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]3=[CH:10][C:9]=2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[C:4]([Cl:35])[CH:3]=1.[NH:36]1[CH:40]=[CH:39][CH:38]=[N:37]1.OC1C=CC=CC=1C=NO.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.C(Cl)Cl.[Cu-]=O>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([C:9]2[CH:10]=[C:11]3[C@H:17]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH2:16][C:15]([CH3:26])([CH3:27])[O:14][C:12]3=[N:13][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([N:36]3[CH:40]=[CH:39][CH:38]=[N:37]3)=[CH:3][C:4]=2[Cl:35])=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 71072739HCID 71072739, compound

Product 1

HCID 91086029HCID 91086029, compound

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of Example 314(280 mg, 0.48 mmol), pyrazole (65.8 mg, 0.97 mmol), copper(I) oxide (3.5 mg, 0.02 mmol), 2-hydroxybenzaldehyde oxime (33.1 mg, 0.24 mmol), and Cs2CO3 (315 mg, 0.97 mmol) in 10 mL of CH3CN was degassed and stirred at 85° C. for 16 h. The reaction mixture was cooled and diluted with CH2Cl2 (50 mL) and filtered through a cake of Celite. The filtrate was washed with H2O (50 mL) and brine (50 mL). After the phases separated, the organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 3:7 v/v EtOAc/hexanes as the eluant afforded the product: 1H NMR δ 1.46 (s, 3H), 1.50 (s, 9H), 1.55 (s, 3H), 1.18 (m, 1H), 2.29 (m, 1H), 4.76 (br. s, 1H), 5.13 (m, 1H), 6.38 (m, 1H), 6.47 (m, 1H), 7.05 (d, J=8.5, 2H), 7.18 (d, J=8.5, 2H), 7.39-7.72 (m, 5H), 7.90 (m, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a cake of Celite
  3. washThe filtrate was washed with H2O (50 mL) and brine (50 mL)
  4. customAfter the phases separated
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customafforded the product

Sources & evidence

ORD record
ord-a2c82d6f1d904bf38c084a09c16ba2b3
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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