Potassium Phosphate, Tribasic → HCID 68966783, compound

HRID 1038134Notes

Reaction equation

HRID 1038134 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[F:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][C:35]=1[OH:43].[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:33][C:34]1[CH:39]=[CH:38][C:37]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[N:4]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)=[CH:36][C:35]=1[OH:43]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 44717470(4-Fluoro-3-hydroxyphenyl)boronic acidHCID 589464433-bromo-5-nitro-1-trityl-1H-indazole

Product 1

HCID 68966783HCID 68966783, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
75 °C

Procedure

A suspension of 3-bromo-5-nitro-1-trityl-1H-indazole 1AJ (10.0 g, 20.68 mmol), 4-fluoro-3-hydroxyphenylboronic acid 6AU (3.55 g, 22.78 mmol), Pd(dppf)Cl2 (1.6 mg, 1.96 mmol) and K3PO4 (10.6 g, 4.99 mmol) in 200 mL of dioxane/H2O (4/1) was heated to 75° C. for overnight. After removal of most of the solvent, the black residue was diluted with EtOAc (250 mL) and H2O (60 mL). The resulting mixture was filtered through a pad of Celite. Additional 150 mL of EtOAc was used to wash the Celite cake. The filtrates were combined. The aqueous layer was separated and the organic layer was washed with brine, dried (MgSO4) and concentrated to give a green solid, which was recrystallized from CH2Cl2/hexane to give 3-(4-fluoro-3-hydroxyphenyl)-5-nitro-1-trityl-1H-indazole 7AU (8.1 g).

Workup

  1. customAfter removal of most of the solvent
  2. additionthe black residue was diluted with EtOAc (250 mL) and H2O (60 mL)
  3. filtrationThe resulting mixture was filtered through a pad of Celite
  4. washto wash the Celite cake
  5. customThe aqueous layer was separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give a green solid, which
  10. customwas recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-f1ca401f066f4cd18c2e5a071d423c76
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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