Water → 7-Bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile

HRID 1896526Notes

Reaction equation

HRID 1896526 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](Cl)=[N:10][CH:11]=[C:12]([C:15]#[N:16])[C:13]=3[S:14][C:4]=2[CH:3]=1.[C:18]([O-:21])([O-])=O.[K+].[K+].O.C[N:26]([CH:28]=O)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([NH:26][CH2:28][C:2]4[CH:7]=[CH:6][C:5]([O:21][CH3:18])=[CH:4][CH:3]=4)=[N:10][CH:11]=[C:12]([C:15]#[N:16])[C:13]=3[S:14][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 59198477HCID 59198477, compound

Product 1

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

Conditions

Temperature
100 °C

Procedure

A mixture of 7-bromo-1-chloro[1]benzothieno[3,2-c]pyridine-4-carbonitrile, 4-methoxybenzyamine (1 equiv) and K2CO3 (1 equiv) in DMF (0.3 M) was heated to 100° C. for 1 h. The mixture was poured into H2O, stirred for 15 min and filtered. The crude product was air dried over night and then heated to reflux in EtOH for 1 h, filtered and washed with EtOH to give the title compound.

Workup

  1. filtrationfiltered
  2. customdried over night
  3. temperatureheated
  4. temperatureto reflux in EtOH for 1 h
  5. filtrationfiltered
  6. washwashed with EtOH

Sources & evidence

ORD record
ord-cebb7c38b14148e4a66418b4a563df37
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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