Sodium Carbonate → Methyl 7-[4-(4-morpholinyl)phenyl]-1-benzothiophene-2-carboxylate

HRID 1012703Notes

Reaction equation

HRID 1012703 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[C:16]2[S:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.[N:21]1([C:27]2[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:21]1([C:27]2[CH:32]=[CH:31][C:30]([C:8]3[C:16]4[S:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][C:12]=4[CH:11]=[CH:10][CH:9]=3)=[CH:29][CH:28]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2795359(4-(Morpholin-4-yl)phenyl)boronic acidHCID 18526159Methyl 7-bromobenzo[b]thiophene-2-carboxylate

Product 1

HCID 58485644Methyl 7-[4-(4-morpholinyl)phenyl]-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3.42 ml of 2 M sodium carbonate solution and 83.5 mg (0.11 mmol) of PdCl2(dppf) are added to a solution of 619.1 mg (2.28 mmol) of methyl 7-bromo-1-benzothiophene-2-carboxylate (Example 6A) and 520 mg (2.51 mmol) of 4-(4-morpholinyl)phenylboronic acid in 10 ml DMF. The mixture is heated at 80° C. for 16 h. Cooling is followed by filtration through kieselguhr and purification by preparative HPLC. The concentrated product is dried under high vacuum. 146.7 mg (16.4% of theory) of the title compound are obtained.

Workup

  1. temperatureCooling
  2. filtrationis followed by filtration through kieselguhr and purification by preparative HPLC
  3. customThe concentrated product is dried under high vacuum

Sources & evidence

ORD record
ord-fe7d48b752474d0fa3b5b594e318660e
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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