Dichloromethane → HCID 89996187, compound

HRID 1480819Notes

Reaction equation

HRID 1480819 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:4]=1[NH2:5].I[C:20]1[CH:21]=[N:22][N:23]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[CH:24]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.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]>[CH3:28][N:27]([CH3:29])[CH2:26][CH2:25][N:23]1[CH:24]=[C:20]([C:8]2[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([O:2][CH3:1])[CH:9]=2)[CH:21]=[N:22]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 644311982-(4-Iodo-1H-pyrazol-1-yl)-N,N-dimethylethan-1-amine

Product 1

HCID 89996187HCID 89996187, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (313 mg, 1.256 mmol), 2-(4-iodo-1H-pyrazol-1-yl)-N,N-dimethylethanamine (Preparation 62, 270 mg, 1.019 mmol) and Pd(dppf)Cl2.DCM (80 mg, 0.098 mmol) was dissolved in THF (4.5 mL) and 2M sodium carbonate in water (1.5 mL) and heated to 60° C. for 18 hours. The mixture was concentrated under reduced pressure. The residue was partitioned between water and DCM and the aqueous layer extracted with DCM three times. The combined organic layers were dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 10% MeOH in DCM to give the title compound (74 mg, 28%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between water and DCM
  3. extractionthe aqueous layer extracted with DCM three times
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-04864b512dd54374a5b06bee5fa981f3
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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