Triethylamine → HCID 66920386, compound

HRID 1510098Notes

Reaction equation

HRID 1510098 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21](Br)=[CH:22][CH:23]=3)[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]=2[O:32][C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[CH3:40])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:5][C:6]([C:21]1[CH:20]=[C:19]2[C:24]([C:16]([C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:13][CH2:12]3)=[O:15])=[C:17]([O:32][C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[N:18]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:23][CH:22]=1)=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 66920372HCID 66920372, compound

Product 1

HCID 66920386HCID 66920386, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of the compound of example 26, step 2, (100 mg, 0.16 mmol), triethylamine (166 mg, 1.6 mmol), 1,3-bis(diphenylphosphino)propane (7.4 mg, 18 μmol) and palladium(II) acetate (3.7 mg, 16 μmol) in DMF (8 ml) and MOH (2 ml) was heated to 120° C. for 2 h under an atmosphere of carbon monoxide. After cooling to room temperature, the mixture was partitioned between water and EA. The aqueous phase was extracted with EA. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (EA/HEP). 30 mg of the title compound were obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between water and EA
  3. extractionThe aqueous phase was extracted with EA
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (EA/HEP)

Sources & evidence

ORD record
ord-037cc4f5cb0549d9bae69eff9d4cf20c
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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