Triethylamine → HCID 18396227, compound

HRID 611573Notes

Reaction equation

HRID 611573 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](I)[C:5]([OH:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:17]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[C:29]#[CH:30])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>CN(C=O)C.CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:17]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[C:29]1[O:8][C:5]2=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:30]=1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 11030701(S)-N-Boc-2-ethynylpyrrolidineHCID 178517758HCID 178517758, compound

Product 1

HCID 18396227HCID 18396227, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

A 3.07 g (12 mmol) sample of 5-chloro-3-iodo-2-pyridinol, from step 13a above, was dissolved in 10 mL of DMF, and (Ph3P)2PdCl2 (0.39 g, 0.5 mmol), CuI (0.38 g, 1.98 mmol) and triethylamine (1.7 mL, 12 mmol) were added. The mixture was stirred under N2 at room temperature for 1 hour, then 1.95 g (10 mmol) of 1-BOC-2-(S)-ethynylpyrrolidine, from Example 1c above, dissolved in 5 mL of DMF, was added carefully. The reaction mixture was stirred at 60° C. for 16 hours, cooled to room temperature, diluted with ether and washed with 50% brine. The organic layer was dried over MgSO4 and concentrated. The residue was chromatographed on silica gel, eluting with 100:0 to 50:50 hexane:EtOAc to give 1.55 g of title compound: MS m/z: 323 (M+H)+.

Workup

  1. additionwas added carefully
  2. stirringThe reaction mixture was stirred at 60° C. for 16 hours
  3. temperaturecooled to room temperature
  4. washwashed with 50% brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 100:0 to 50:50 hexane

Sources & evidence

ORD record
ord-2a17af0222d141b9affb3a32128b4430
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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