Hydrochloric Acid → HCID 86620841, compound

HRID 2076330Notes

Reaction equation

HRID 2076330 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([C:21]#[N:22])=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Br)=[CH:26][CH:25]=1.Cl.[OH-].[Na+]>C1COCC1>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:21](=[NH:22])[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18]=2[CH:19]=[CH:20][C:11]([NH:10][C@H:1]2[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]2)=[N:12]3)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67096021HCID 67096021, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 86620841HCID 86620841, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (ice bath) and stirred suspension of 2-((R)-indan-1-ylamino)-quinoline-5-carbonitrile (example 80, step A) (285 mg, 1.0 mmol) in THF (5 ml) was added drop wise a 1M solution of 4-fluorophenyl-magnesium bromide (6 ml, 6.0 mmol), the reaction mixture was heated under reflux conditions for 92 h and poured into ice-water (20 ml). 2N HCl (5 ml) was added, the mixture was stirred at room temperature for 10 min, 3 N NaOH (5 ml) was added and the mixture was extracted with ethyl acetate (3×80 ml). The combined organic layers were washed with brine (2×50 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield the title compound as light red foam (210 mg, 55%).

Workup

  1. temperatureTo a cooled (ice bath)
  2. temperaturethe reaction mixture was heated under reflux conditions for 92 h
  3. stirringthe mixture was stirred at room temperature for 10 min
  4. extractionthe mixture was extracted with ethyl acetate (3×80 ml)
  5. washThe combined organic layers were washed with brine (2×50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record
ord-a657bdc8eb5e401dacb672fcf687c240
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

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