Hydrochloric Acid → HCID 18405252, compound

HRID 1017731Notes

Reaction equation

HRID 1017731 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[C:9]2[CH:20]=[C:21](Br)[S:22][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.Cl>C(O)C.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[CH2:11][N:10]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][C:8]2[S:22][C:21]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)=[CH:20][C:9]1=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 27339602-Thiopheneboronic acidHCID 9845714HCID 9845714, compound

Product 1

HCID 18405252HCID 18405252, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakis-(triphenylphosphine)palladium (0) (20 mg) was added to a degassed solution of ethyl4-(3,4-dichlorobenzyl)-2-bromothieno[3,2-b]pyrrole-5-carboxylate (0.1 g) and thiophene-2-boronic acid (34 mg) in ethanol (1 ml), toluene (1 ml) and aqueous potassium carbonate (2N, 1 ml), and the reaction stirred at 80° C. under an argon atmosphere for 6 hours. The reaction was cooled, poured into 2N HCl and extracted with ether. Combined organic extracts were cried (MgSO4), concentrated in vacuo and the residue purified by column chromatography using isohexane to isohexane-25% ethyl acetate as eluent to give the product as a pale yellow crystalline solid (77 mg, 77%), M/z (+) 435 (MH+), 276, 204, 159, 127.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ether
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-0b9dc076f2a34edcb6804d4e07bfcb22
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

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