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Potassium Phosphate, Tribasic → tert-butyl 4-(5,6-difluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazole-1-carboxylate

HRID 2274775
Notes
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Reaction equation

HRID 2274775 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[C:5]2I.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[N:32][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:34]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[C:5]2[C:30]1[CH:31]=[N:32][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:34]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 1180602835,6-difluoro-3-iodo-1-(phenylsulfonyl)-1H-indole2×

Product 1

HCID 118059922tert-butyl 4-(5,6-difluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazole-1-carboxylateYield 62%

Reagents, catalysts & solvents 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5,6-difluoro-3-iodo-1-(phenylsulfonyl)-1H-indole (Intermediate 28; 300 mg; 0.716 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (273.6 mg; 0.93 mmol), K3PO4 (455 mg; 2.15 mmol) in dioxane (10 mL) and water (1 mL) was added Pd(dppf)Cl2 (59 mg; 0.072 mmol) under argon. The reaction mixture was stirred at 90° C. for 12 hours. The mixture was filtered through Celite and washed with EtOAc (50 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, concentrated, and purified by a silica gel chromatography (petroleum ether/EtOAc=1/1) to afford 203 mg (62%) of the title compound as a yellow solid.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with EtOAc (50 mL)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified by a silica gel chromatography (petroleum ether/EtOAc=1/1)

Sources & evidence

ORD record
ord-1901090ae2f84fbc9fc0c5c3a4bdfa9a
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09126984B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes