Triethylamine → HCID 178471066, compound

HRID 2289973Notes

Reaction equation

HRID 2289973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](I)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:32]([O:36][CH2:37][CH3:38])(=[O:35])[CH:33]=[CH2:34].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](/[CH:34]=[CH:33]/[C:32]([O:36][CH2:37][CH3:38])=[O:35])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 178522917HCID 178522917, compound

Product 1

HCID 178471066HCID 178471066, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the title compound of Example 5 (1.05 g), triethylamine (6 mL), ethyl acrylate (0.3 mL), palladium acetate (5.1 mg) and tris(o-tolyl)phosphine (42 mg) in DMF (5 mL) is heated to 100° C. for 24 h in a pressure-safe tube. The reaction is partitioned between CH2Cl2 and water. The aqueous layer is extracted with CH2Cl2 (3×). The combined organic layers are filtered, dried over Na2SO4, filtered and condensed. The crude product is purified by trituration with hot EtOAc to yield 0.461 g of the desired product as a tan solid.

Workup

  1. customThe reaction is partitioned between CH2Cl2 and water
  2. extractionThe aqueous layer is extracted with CH2Cl2 (3×)
  3. filtrationThe combined organic layers are filtered
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customcondensed
  7. customThe crude product is purified by trituration with hot EtOAc

Sources & evidence

ORD record
ord-e87433d1dec84b8fb87efb34147786ee
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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