Methyl 2-(2,5-dimethoxy-tetrahydrofuran-3-yl)acetate → 2-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-acetic acid methyl ester

HRID 382192Notes

Reaction equation

HRID 382192 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13](F)=[CH:12][CH:11]=2)[CH:6]=1.N[C:19]1([C:31]#[N:32])[CH:24]=[CH:23][C:22](C2C=CC=CC=2)=[CH:21][CH2:20]1.COC1C(CC(OC)=O)CC(OC)O1>CCOC(C)=O.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([C:22]3[CH:23]=[CH:24][C:19]([C:31]#[N:32])=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 18380381Methyl 2-(2,5-dimethoxy-tetrahydrofuran-3-yl)acetateHCID 543331132-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid methyl esterHCID 674040024-Amino-4-cyano-biphenyl

Product 1

HCID 183415162-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-acetic acid methyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

According to the procedure described in Example 14(a) for the preparation of 2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid methyl ester, 4-amino-4-cyano-biphenyl (commercially available from TCI) and methyl 2-(2,5-dimethoxy-tetrahydrofuran-3-yl)acetate were condensed in 6 hours at 80° C. to give a crude product. Successive flash column chromatography with EtOAc/CH2Cl2/hex gave in 60% yield 2-[1-(4′-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-acetic acid methyl ester as an amorphous solid.

Workup

  1. customcondensed in 6 hours at 80° C.
  2. customto give a crude product

Sources & evidence

ORD record
ord-cb787cd935364fecba8cb7cccbbabe1e
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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