Dimethylformamide → HCID 68712754, compound

HRID 1896532Notes

Reaction equation

HRID 1896532 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([NH:17]CC4C=CC(OC)=CC=4)=[N:10][CH:11]=[C:12]([C:15]#[N:16])[C:13]=3[S:14][C:4]=2[CH:3]=1.[CH3:27][N:28](C=O)C>[C-]#N.[C-]#N.[Zn+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>[NH2:17][C:9]1[C:8]2[C:5]3[CH:6]=[CH:7][C:2]([C:27]#[N:28])=[CH:3][C:4]=3[S:14][C:13]=2[C:12]([C:15]#[N:16])=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 591984657-Bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile

Product 1

HCID 68712754HCID 68712754, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a microwave reaction vessel was added 7-bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile (Example 12, Step 9), Zn(CN)2 (1.3 equiv), Pd(Ph3P)4 (0.1 equiv), and DMF (0.06 M). After sealing, the tube was degassed via a needle through the septum, and the reaction was set up on the Smith Creator microwave machine for 5 min at 150° C. The mixture was then added to H2O and the resulting solid was collected by filtration and dried under vacuum. The crude was then stirred with 1:10 EtOAc:hexanes containing a trace of acetone, to give after filtration, a pale brown solid which was used as such for the next step.

Workup

  1. customTo a microwave reaction vessel
  2. customthe tube was degassed via a needle through the septum
  3. additionThe mixture was then added to H2O
  4. filtrationthe resulting solid was collected by filtration
  5. customdried under vacuum
  6. customhexanes containing a trace of acetone, to give
  7. filtrationafter filtration

Sources & evidence

ORD record
ord-ed202490c150402aa9866d493e8ee7cb
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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