5-(4-Chloro-phenyl)-2-ethynyl-pyridine → HCID 57845314, compound

HRID 734869Notes

Reaction equation

HRID 734869 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[CH:24][C:25]([C:28]#[CH:29])=[N:26][CH:27]=2)=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:23]=[CH:24][C:25]([C:28]#[C:29][C:2]3[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C@@H:10]4[CH2:14][CH2:13][CH2:12][NH:11]4)=[CH:4][CH:3]=3)=[N:26][CH:27]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridineHCID 69055318HCID 69055318, compound

Product 1

HCID 57845314HCID 57845314, compound

Procedure

The product was obtained analogously to Example 7.1e starting from (4-iodophenyl)-(S)-1-pyrrolidin-2-ylmethylamine and 5-(4-chlorophenyl)-2-ethynylpyridine. The crude product was purified by MPLC (Hyperprep HS C18, 8 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v). The eluates were evaporated down in vacuo and the residue was neutralized with sat. aqueous sodium bicarbonate solution. The aqueous phase was extracted with DCM, dried over magnesium sulfate and evaporated down in vacuo. Yield: 35 mg (11% of theoretical); C24H22ClN3 (M=387.904); calc.: molpeak (M+H)+:388/390 (Cl); found: molpeak (M+H)+:388/390 (Cl); HPLC-MS: 5.0 minutes (method B).

Workup

  1. customThe product was obtained analogously to Example 7.1e
  2. customThe crude product was purified by MPLC (Hyperprep HS C18, 8 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v)
  3. customThe eluates were evaporated down in vacuo
  4. extractionThe aqueous phase was extracted with DCM
  5. dry with materialdried over magnesium sulfate
  6. customevaporated down in vacuo
  7. custom5.0 minutes (method B)

Sources & evidence

ORD record
ord-f251895726de4281b86db2e966b8f594
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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