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Potassium Phosphate, Tribasic → N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide

HRID 593694
Notes
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Reaction equation

HRID 593694 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:18])=[N:4][N:3]=1.[C:19]([NH:23][S:24]([C:27]1[CH:28]=[N:29][CH:30]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:32]=1)(=[O:26])=[O:25])([CH3:22])([CH3:21])[CH3:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C([O-])=O.[NH4+].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[C:19]([NH:23][S:24]([C:27]1[CH:28]=[N:29][CH:30]=[C:31]([C:2]2[C:11]3[C:6](=[C:7]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:8]=[CH:9][CH:10]=3)[C:5]([Cl:18])=[N:4][N:3]=2)[CH:32]=1)(=[O:26])=[O:25])([CH3:22])([CH3:20])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 90386425N-(tert-Butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamideHCID 904244121,4-Dichloro-5-phenylphthalazine

Product 1

HCID 90424399N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamideYield 76.1%

Reagents, catalysts & solvents 5

HCID 75806
Tricyclohexylphosphine
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent
HCID 2723923Ammonium formateSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1,4-dichloro-5-phenylphthalazine (0.400 g, 1.45 mmol) and N-(tert-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide (0.742 g, 2.18 mmol) (Johnson et al., WO 2011/28741) in 1,4-dioxane (15 mL) and water (3 mL) was added K3PO4 (0.617 g, 2.91 mmol) and the contents purged with nitrogen for 10 min. Tricyclohexylphosphine (10.2 mg, 0.0360 mmol) was added followed by Pd2(dba)3 (0.0130 g, 0.0150 mmol) and heated at 95° C. for 12 h. The reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with HCOONH4 buffer (pH˜5) solution and extracted with EtOAc (3×75 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by combiflash (REDISEP®, silica gel, 12 g, 30% EtOAc/hexanes) to obtain N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide (0.500 g, 76.0%) as a pale yellow solid. LCMS (Condition 11): retention time 1.04 min, [M+1]=453.2. 1H NMR (400 MHz, DMSO-d6) δ 1.20 (s, 9 H), 7.43-7.46 (m, 2 H), 7.50-7.54 (m, 3 H), 7.98 (s, 1 H), 7.99 (dd, J=1.2 Hz, J=8.0 Hz, 1H), 8.03 (dd, J=1.2 Hz, J=7.2 Hz, 1 H), 8.15 (dd, J=7.2 Hz, J=8.0 Hz, 1 H), 8.58 (t, J=2.0 Hz, 1 H), 9.17 (d, J=2.0 Hz, 1 H), 9.23 (d, J=2.0 Hz, 1 H).

Workup

  1. customthe contents purged with nitrogen for 10 min
  2. temperatureto cool to ambient temperature
  3. extractionextracted with EtOAc (3×75 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by combiflash (REDISEP®, silica gel, 12 g, 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8fe2ec71ce164915917a24db71f61151
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242966B2

Reaction notes

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