Dichloromethane → HCID 67343116, compound

HRID 2038461Notes

Reaction equation

HRID 2038461 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2OS(C(F)(F)F)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>CCOC(C)=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].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.[Fe+2].O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:28])[CH:34]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27339503-Tolylboronic acidHCID 87364079HCID 87364079, compound

Product 1

HCID 67343116HCID 67343116, compoundYield 72.3%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To the title compound of Step A (0.12 g, 0.27 mmol), 3-methylphenylboronic acid (0.08 g, 0.60 mmol), K3PO4 (0.128 g, 0.54 mmol), Pd(dppf)Cl2.CH2Cl2 (0.013 g, 0.017 mmol) and dppf (0.006 g, 0.010 mmol) was added dioxane (3 mL). The flask was heated at 100° C. for 18 h, cooled to rt, diluted with EtOAc and filtered through a small silica pad. Silica gel chromatography (10-40% EtOAc in hexanes) gave 0.073 g (72% yield) of the title compound. 1H NMR (CDCl3): 7.31-7.26 (m, 4H), 7.18-7.15 (m, 1H), 7.05 (dd, J=8.2, 2.0 Hz, 1H), 6.57 (d, J=1.9 Hz, 1H), 4.86-4.81 (m, 1H), 4.30-4.26 (m, 2H), 3.96 (dd, J=10.2, 4.2 Hz, 2H), 2.40 (s, 3H), 1.44 (s, 9H).

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered through a small silica pad

Sources & evidence

ORD record
ord-e878a5fe966646bcb1392e625e0e6ab5
Source dataset
uspto-grants-2013_11
Patent number
US08575364B2

Reaction notes

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