Hydrochloric Acid → Methyl 4'-[[3-butyl-4-quinolinyl]-methyl](1,1'-biphenyl)-2-carboxylate

HRID 398988Notes

Reaction equation

HRID 398988 reaction equation
BrC[C:3]1[CH:4]=[C:5]([C:15]([O:17][CH3:18])=[O:16])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.[CH2:19]([C:23]1[CH:24]=[N:25][C:26]2[C:31]([C:32]=1Cl)=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:21][CH3:22].Cl.O1CCC[CH2:36]1>[Zn].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:19]([C:23]1[CH:24]=[N:25][C:26]2[C:31]([C:32]=1[CH2:36][C:12]1[CH:13]=[CH:14][C:9]([C:6]3[C:5]([C:15]([O:17][CH3:18])=[O:16])=[CH:4][CH:3]=[CH:8][CH:7]=3)=[CH:10][CH:11]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 19595328Methyl 4-(bromomethyl)(1,1'-biphenyl)-2-carboxylateHCID 195953523-Butyl-4-chloro quinoline

Product 1

HCID 19595364Methyl 4'-[[3-butyl-4-quinolinyl]-methyl](1,1'-biphenyl)-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

475 mg of electrolytic zinc, 275 mg of tetrakis (triphenylphosphine) palladium, 2.08 g of methyl 4-(bromomethyl)-1,1-biphenyl-2-carboxylate (prepared in EP 0,025,331)) were introduced into 13 ml of tetrahydrofuran. 503 mg of 3-butyl-4-chloro quinoline of Step F were introduced and the mixture was stirred for 15 hours in an ultrasonic bath, allowing the temperature to rise to 65° C. 50 ml of 0.1N hydrochloric acid were added and extraction was carried out with ethyl acetate. The extracts were washed with a saturated solution of sodium chloride, dried and evaporated to dryness. After chromatography on silica (eluant: choloroform-hexane-ethyl acetate 100-100-10), 624 mg of the expected product were obtained.

Workup

  1. customto rise to 65° C
  2. extractionextraction
  3. washThe extracts were washed with a saturated solution of sodium chloride
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-29fac6e59a534c9f8a5507b42921437f
Source dataset
uspto-grants-1998_10
Patent number
US05817674

Reaction notes

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