Zinc → HCID 178497614, compound

HRID 398996Notes

Reaction equation

HRID 398996 reaction equation
[Zn:1].[Br:2]C[C:4]1[CH:5]=[C:6]([C:16]([O:18][CH3:19])=[O:17])[C:7](C2C=CC=CC=2)=[CH:8][CH:9]=1.ClC1C2C(=CC=CC=2)N=[C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)N=1>O1CCCC1>[Br-:2].[CH3:19][O:18][C:16]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:4][C:5]=1[C:34]1[CH:33]=[CH:32][C:31]([CH2:23][Zn+:1])=[CH:36][CH:35]=1)=[O:17]

Participants

5

Reactant 3

HCID 23994ZincHCID 809774-Chloro-2-phenylquinazolineHCID 19595328Methyl 4-(bromomethyl)(1,1'-biphenyl)-2-carboxylate

Product 1

HCID 178497614HCID 178497614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[[2'-(methoxycarbonyl)(1,1'-biphenyl)-4-yl]-methyl]zinc bromide was prepared in advance from 400 mg of zinc in 1 ml of tetrahydrofuran and 1.53 g of methyl 4-(bromomethyl)(1,1'-biphenyl)-2-carboxylate (KNOCHEL, J. Org. Chem., 1988, Vo. 53, p. 5789 to 5791) and 240.69 mg of 4-chloro-2-phenyl-quinazoline and 115 mg of palladium tetrakis(triphenyl-phosphine) complex were added to the solution. The mixture stood at 50° C. for 6 hours and the reaction medium was poured into a water/ice/acetic acid mixture. The aqueous phase was extracted with ethyl acetate and the organic phase was washed with water and water saturated with sodium chloride, dried and evaporated. After chromatography on silica (eluant:ethyl acetate-hexane 1-9 then 2-8), 260 mg of expected product melting at 120° C. to 121° C. after crystallization from isopropyl ether were obtained.

Workup

  1. additionwere added to the solution
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe organic phase was washed with water and water saturated with sodium chloride
  4. customdried
  5. customevaporated
  6. customAfter chromatography on silica (eluant:ethyl acetate-hexane 1-9 then 2-8), 260 mg of expected product melting at 120° C. to 121° C. after crystallization from isopropyl ether
  7. customwere obtained

Sources & evidence

ORD record
ord-27047be21b884980abc838eabf5dd9ae
Source dataset
uspto-grants-1998_10
Patent number
US05817674

Reaction notes

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