Dichloromethane → HCID 22147956, compound

HRID 1823918Notes

Reaction equation

HRID 1823918 reaction equation
[I:1][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]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[N:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].ClCCl.[Cl-].[NH4+]>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].C(COC)OC>[I:1][C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[NH:3]1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 22147941HCID 22147941, compound

Product 1

HCID 22147956HCID 22147956, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 3-iodo-1-(2-methoxyethoxymethyl)-5-nitro-1H-indazole (0.50 g, 1.32 mmol), phenyl boronic acid (0.22 g, 1.80 mmol), potassium phosphate (1.26 g, 5.94 mmol) and 1,1′-Bis(diphenylphosphino)ferrocenedichloropalladium(II), complex with dichloromethane (0.15 g, 0.18 mmol) was added dry dimethoxyethane (8.0 ml) and then heated at 85° C. for 18 hours. Ammonium chloride solution (30 ml, saturated aqueous) was added and extracted into ethyl acetate (3×30 ml). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (3% MeOH in DCM) to afford the title compound as a yellow solid (0.35 g, 81%). 1H NMR (400 MHz, CDCl3) δ 3.37 (3H, s), 3.51–3.53 (2H, m), 3.73–3.75 (2H, m), 5.93 (1H, s), 7.50–7.54 (1H, m), 7.57–7.61 (2H, m), 7.73 (1H, d), 7.98 (2H, dd), 8.37 (1H, dd), 9.00 (1H, s).

Workup

  1. extractionextracted into ethyl acetate (3×30 ml)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (3% MeOH in DCM)

Sources & evidence

ORD record
ord-ba0671058e5d43e6a08e1e580e4b0c6c
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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