Dimethylformamide → HCID 59860358, compound

HRID 252136Notes

Reaction equation

HRID 252136 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:5]=1[CH2:6][NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][N:14]=2)[CH2:9]1.[CH2:25](B(CC)CC)[CH3:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[Cl:3][C:4]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:5]=1[CH2:6][NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:25][CH3:26])=[CH:15][N:14]=2)[CH2:9]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7357TriethylboraneHCID 11430Potassium CarbonateHCID 66856259HCID 66856259, compound

Product 1

HCID 59860358HCID 59860358, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Add (2,4-dichlorobenzyl)-[1-(5-iodopyridin-2-yl)-pyrrolidin-3-yl]-amine dihydrochloride (272 mg, 0.61 mmol), triethylborane (1 mL, 1 mmol, 1.0 M in hexanes), tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.031 mmol), and potassium carbonate (253 mg, 1.83 mmol) to anhydrous N,N-dimethylformamide (10 mL). Heat at 65° C. overnight. Dilute with water and extract twice with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate), filter, concentrate to give a residue. Chromatograph the residue on silica gel eluting with 10:90 to 1:1 ethyl acetate:hexanes, to give the title compound. Combine the title compound and ethyl acetate, add 1 N hydrochloric acid in methanol (1 mL), and concentrate to give the title compound as the hydrochloride salt (35 mg, 13%). 1H NMR (400 MHz, MeOH-d4) δ 7.98 (d, 1H, J=8.8 Hz), 7.80 (s, 1H), 7.69-7.67 (m, 2H), 7.49 (dd, 1H, J=8.0, 2.2 Hz), 7.09 (d, 1H, J=8.8 Hz), 4.50-4.42 (m, 2H), 4.25-4.22 (m, 1H), 4.10-4.05 (m, 1H), 3.90-3.84 (m, 2H), 3.74-3.68 (m, 1H), 2.71-2.61 (m, 1H), 2.64 (q, 2H, J=7.2 Hz), 2.47-2.41 (m, 1H), 1.24 (t, 3H, J=7.2 Hz); MS (ES): m/z=350 [M+H].

Workup

  1. extractionextract twice with ethyl acetate
  2. washWash the organic layer with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give a residue

Sources & evidence

ORD record
ord-65cfded072994bb2832d5fdca0141a35
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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