Potassium Hydroxide → HCID 59627924, compound

HRID 2421244Notes

Reaction equation

HRID 2421244 reaction equation
Br[C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=1.[OH-:26].[K+].P.CC(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)C>O1CCOCC1.ClCCl.O.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]>[F:11][C:9]1[CH:10]=[C:2]([OH:26])[C:3]2[CH:4]=[CH:5][N:6]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:14][CH:13]=3)[C:7]=2[CH:8]=1

Participants

9

Reactant 4

HCID 14797Potassium HydroxideHCID 24404PhosphineHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 596279334-Bromo-6-fluoro-1-[4-(phenylmethoxy)phenyl]-1H-indole

Product 1

HCID 59627924HCID 59627924, compoundYield 44.6%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-bromo-6-fluoro-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indole (D19) (200 mg, 0.505 mmol) and potassium hydroxide (113 mg, 2.02 mmol) in 1,4-dioxan (3 mL)/water (3 mL) was treated with Pd2dba3 (9 mg, 0.02 mmol) and phosphine ligand, bis(1,1-dimethylethyl)[2′,4′,6′-tris(1-methylethyl)-2-biphenylyl]phosphane (11 mg, 0.05 mmol) and the mixture was heated to 85° C. for 1.5 hours. After cooling, the mixture was diluted with dichloromethane and water and the product was extracted into dichloromethane. The combined organic layers were dried (MgSO4) and evaporated. Chromatography on silica gel (elution with 0-50% ethyl acetate in hexane) gave the title compound (D20), (75 mg).

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted into dichloromethane
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-015c562cae714ff8a34db46a2809a9c4
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

Loading…