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Dichloromethane → HCID 18446586, compound

HRID 1868329
Notes
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Reaction equation

HRID 1868329 reaction equation
[C:1]([C:3]1[C:4]2[S:12][C:11](Br)=[CH:10][C:5]=2[C:6](=[O:9])[NH:7][CH:8]=1)#[N:2].[C:14]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C=O)C.O.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]>[C:1]([C:3]1[C:4]2[S:12][C:11]([C:21]3[CH:22]=[CH:23][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=3)=[CH:10][C:5]=2[C:6](=[O:9])[NH:7][CH:8]=1)#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 184465192-Bromo-4-oxo-4,5-dihydrothieno[3,2-c]pyridine-7-carbonitrile

Product 1

HCID 18446586HCID 18446586, compoundYield 57.9%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 7-cyano-2-bromo-4-oxo-4,5-dihydrothieno[3,2-c]-pyridine (2.0 g, 7.84 mmol) in DMF (40 mL) and water (15 mL) was added 4-t-butylphenyl boronic acid (2.1 g, 11.8 mmol), potassium carbonate (1.4 g, 10.1 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.192 g, 0.23 mmol). The resulting mixture was stirred under nitrogen for 4 h at 80° C. After this time the mixture was diluted with DMF (20 mL), filtered through celite to remove palladium residues and water (100 mL) added. The precipitated solid was filtered, washed thoroughly with water and dried in air by suction at room temperature providing 1.4 g of 100 which was used without further analysis or purification.

Workup

  1. filtrationfiltered through celite
  2. customto remove palladium residues and water (100 mL)
  3. additionadded
  4. filtrationThe precipitated solid was filtered
  5. washwashed thoroughly with water
  6. customdried in air by suction at room temperature

Sources & evidence

ORD record
ord-251758f11325475995ea83627c83fe3d
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07635695B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes