Ethyl 4-cyano-5-(methylsulfonyl)-3-phenylthiophene-2-carboxylate → Ethyl 4-cyano-5-((3,5-dichloropyridin-4-yl)thio)-3-phenylthiophene-2-carboxylate

HRID 1192255Notes

Reaction equation

HRID 1192255 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[S:6][C:7]=1[S:8]([CH3:11])(=O)=O)#[N:2].[Na].[Cl:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([Cl:32])C=1S>>[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[S:6][C:7]=1[S:8][C:11]1[C:25]([Cl:24])=[CH:26][N:27]=[CH:28][C:29]=1[Cl:32])#[N:2]

Participants

3

Reactant 2

HCID 60207473Ethyl 4-cyano-5-(methylsulfonyl)-3-phenylthiophene-2-carboxylateHCID 178527724HCID 178527724, compound

Product 1

HCID 60207474Ethyl 4-cyano-5-((3,5-dichloropyridin-4-yl)thio)-3-phenylthiophene-2-carboxylate

Procedure

Prepared according to the procedure described for step C of example 18 from Ethyl 4-cyano-5-(methylsulfonyl)-3-phenylthiophene-2-carboxylate (0.3 g, 0.89 mmol) from above and 3,5-dichloropyridine-4-thiol sodium salt (0.18 g, 1.0 mmol) at 90° C. for over night. The title product was obtained as a white solid. The crude product was used as such for the next step transformation. MS m/z: 434.98, 436.98 [M+H]+.

Workup

  1. customPrepared
  2. customat 90° C.

Sources & evidence

ORD record
ord-8cb2ccb51afc4a76b250a2c71442fb5c
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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