Triethylamine → HCID 57754479, compound

HRID 226260Notes

Reaction equation

HRID 226260 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:15][CH2:14][C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[CH:7]([OH:16])[C:6]=2[CH:17]=1.[F:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[F:29])[N:25]=[C:24]([CH:30]=[CH2:31])[CH:23]=[CH:22]2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[F:29])[N:25]=[C:24](/[CH:30]=[CH:31]/[C:2]1[CH:3]=[CH:4][C:5]3[O:15][CH2:14][C:9]4=[N:10][CH:11]=[CH:12][CH:13]=[C:8]4[CH:7]([OH:16])[C:6]=3[CH:17]=1)[CH:23]=[CH:22]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 9971554HCID 9971554, compoundHCID 17837600HCID 17837600, compound

Product 1

HCID 57754479HCID 57754479, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

0.37 g (1.26 mmol) of the bromo derivative of step 3 are mixed with 0.27 g (1.41 mmol) of the vinyl derivative of step 4, 8.5 mg (0.0378 mmol) of palladium acetate and 36.2 mg (0.118 mmol) of tri(o-tolyl)phosphine in 2.5 ml of DMF. The solution is degassed and cooled with an ice bath. In a nitrogen atmosphere it is dropped inside a solution of 0.27 ml (0.196 g; 1.937 mmol) of N,N,N-triethylamine in 1.2 ml DMF. The whole is stirred at 100° C. for 1 hr. Once at room temperature, 4 ml of water are dropped inside and the solid is filtered, washed with water and dried. The yield is 0.5 g (98%).

Workup

  1. customThe solution is degassed
  2. temperaturecooled with an ice bath
  3. filtrationthe solid is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2c3ab122070f4ca2a464c57cd8a924c1
Source dataset
uspto-grants-2009_07
Patent number
US07557212B2

Reaction notes

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