Dimethylformamide → HCID 59198475, compound

HRID 1896539Notes

Reaction equation

HRID 1896539 reaction equation
[CH3:1][C:2]([O-:4])=[O:3].[Na+].BrC1[CH:12]=[CH:11][C:10]2[C:13]3[C:14]([NH:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[N:15][CH:16]=[C:17]([C:20]#[N:21])[C:18]=3[S:19][C:9]=2[CH:8]=1.[CH3:32]N(C=O)C.[C]=O>CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[C:20]([C:17]1[C:18]2[S:19][C:9]3[CH:8]=[C:1]([C:2]([O:4][CH3:32])=[O:3])[CH:12]=[CH:11][C:10]=3[C:13]=2[C:14]([NH:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[N:15][CH:16]=1)#[N:21]

Participants

10

Reactant 4

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 591984657-Bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrileHCID 178418416HCID 178418416, compound

Product 1

HCID 59198475HCID 59198475, compound

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of Pd(OAc)2 (0.26 equiv), Pd(Ph3P)4 (0.30 equiv), NaOAc (1.7 equiv) and 7-bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile (Example 12, Step 9) in a 1:1 (v/v) mixture of DMF and MeOH (1 M) was stirred at 110° C. under 160 psig of carbon monoxide in a sealed bomb for 18 h. The reaction media was poured in EtOAc and diluted with H2O. The phases were separated and the organic layer washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography using EtOAc and hexanes gradient to yield the title compound.

Workup

  1. customThe reaction media
  2. customThe phases were separated
  3. washthe organic layer washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-cadb630551fc4f44a491a35b98d75613
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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