Triethylamine → HCID 68916511, compound

HRID 2217467Notes

Reaction equation

HRID 2217467 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][CH:9]1[C:21]([OH:23])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:24][C:25]1[CH:31]=[C:30]([I:32])[CH:29]=[CH:28][C:26]=1[NH2:27].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[C:21](=[O:23])[NH:27][C:26]1[CH:28]=[CH:29][C:30]([I:32])=[CH:31][C:25]=1[F:24])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 1856942-Fluoro-4-iodoanilineHCID 22028680HCID 22028680, compound

Product 1

HCID 68916511HCID 68916511, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (0.673 g, 1.94 mmol), 2-fluoro-4-iodoaniline (0.46 g, 1.94 mmol), EEDQ (0.575 g, 2.32 mmol) and triethylamine (0.408 mL, 2.91 mmol) were heated at reflux in CHCl3 (10 mL) for 22 h. The solution was concentrated and resulting oil partitioned between EtOAc and water. The organic layer was washed with brine and dried over MgSO4. The product was purified by mplc to produce the product as a clear oil (1.0 g, 90%). MS: APCI (AP−): 563.2 (M)−.

Workup

  1. concentrationThe solution was concentrated
  2. customresulting oil
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe product was purified by mplc

Sources & evidence

ORD record
ord-ef48c1b80db945f4b1889eb153c20701
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

Loading…