Triethylamine → HCID 86728176, compound

HRID 1848378Notes

Reaction equation

HRID 1848378 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.[C:28]([O:36][CH3:37])(=[O:35])[C:29]#[C:30][C:31]([O:33][CH3:34])=[O:32].C(N(CC)CC)C.Cl[C:46](=[O:52])[C:47]([O:49][CH2:50][CH3:51])=O>C(Cl)Cl.CCOC(C)=O>[CH2:50]([O:49][C:47]1[C:46](=[O:52])[N:25]([C:24]2[CH:26]=[CH:27][C:21]([F:20])=[CH:22][CH:23]=2)[CH:30]([C:31]([O:33][CH3:34])=[O:32])[C:29]=1[C:28]([O:36][CH3:37])=[O:35])[CH3:51]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 11776TriphenylphosphineHCID 12980Dimethyl acetylenedicarboxylateHCID 20884Ethoxalyl chloride

Product 1

HCID 86728176HCID 86728176, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of triphenylphosphine (262 mg, 1.00 mmol) and 4-fluoroaniline (111 mg, 1.00 mmol) in CH2Cl2 (5 mL) was added dimethyl but-2-ynedioate (142 mg, 1.00 mmol) dropwise. The reaction mixture turned brown and was stirred for 1 h before triethylamine (139 μL, 1.00 mmol) and ethyl 2-chloro-2-oxoacetate (150 mg, 1.10 mmol) were added. The reaction mixture was stirred at rt for 14 h, concentrated and the residue was purified by ISCO, eluting with Hex/EtOAc (0-20% B over 15 min) to Intermediate 12 (180 mg, 0.530 mmol, 53.0% yield) as a white solid. HPLC/MS (Method L) RT=1.75 min, [M+H]+ 337.9.

Workup

  1. additionwere added
  2. concentrationconcentrated
  3. customthe residue was purified by ISCO

Sources & evidence

ORD record
ord-96d327a923f046a1a9fec573579e14ee
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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