Triethylamine → HCID 67361188, compound

HRID 1951362Notes

Reaction equation

HRID 1951362 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[C:12]([CH3:14])[N:13]=[C:7]2[C:6]=1I)[CH:2]=[CH2:3].CCN(CC)CC>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH3:14][C:12]1[CH2:11][N:8]2[CH:9]=[CH:10][C:5]3[C:6]([C:2]([CH3:3])=[CH:1][N:4]=3)=[C:7]2[N:13]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 67377459HCID 67377459, compound

Product 1

HCID 67361188HCID 67361188, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 30 (117 mg, 0.37 mmol), anhydrous DMF (5 mL), Et3N (130 μL, 0.94 mmol), tetrabutylammonium chloride (104 mg, 0.37 mmol), Pd(OAc)2 (9 mg, 40.1 μmol) was stirred for 3 days at room temperature. After removal of the solvent, the residue was diluted with H2O (10 mL), basified with Na2CO3 to pH=10-12 and extracted with CH2Cl2 (3×20 mL). The CH2Cl2 extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford compound 31 (26 mg, yield: 38%); mp 211° C.; IR (KBr) 3099, 3068, 3006, 2913, 2858, 1633, 1517 cm−1; 1H NMR (400 MHz, CDCl3) δ 2.45 (s, 3H), 2.61 (s, 3H), 6.78 (d, 1H, J=7.2 Hz), 6.90 (s, 1H), 7.22 (s, 1H), 7.66 (d, 1H, J=7.2 Hz), 9.55 (brs, 1H); 13C NMR (100 MHz, CDCl3) δ 11.9, 14.3, 101.5, 109.0, 113.3, 113.7, 119.8, 120.6, 131.1, 140.0, 142.6. Anal. Calcd for C11H11N3: C, 71.33; H, 5.99; N, 22.69. Found: C, 70.94; H, 5.89; N, 23.01.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was diluted with H2O (10 mL)
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe CH2Cl2 extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-b9705f7990414d7c85d4a3707a7a5a7c
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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