Tert-butyl 4-(4-amino-7-bromothieno[3,2-c]pyridin-3-yl)phenylcarbamate → 3-(4-Aminophenyl)-7-bromothieno[3,2-c]pyridin-4-amine

HRID 2390626Notes

Reaction equation

HRID 2390626 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([Br:25])=[CH:4][N:3]=1>C(O)(C(F)(F)F)=O.ClCCl>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([Br:25])[C:6]=3[S:10][CH:9]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 18451459Tert-butyl 4-(4-amino-7-bromothieno[3,2-c]pyridin-3-yl)phenylcarbamate

Product 1

HCID 184507463-(4-Aminophenyl)-7-bromothieno[3,2-c]pyridin-4-amineYield 94.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Example 76B (0.5 g, 1.1 mmol) in TFA (4 mL) and dichloromethane (5 mL) was stirred at 0° C. for 5 minutes, warmed to room temperature for 2 hours, then concentrated. The residue was dissolved in dichloromethane, washed with brine, dried (Na2SO4), filtered, and concentrated to provide 0.332 g of the desired product. MS (ESI(+)) m/e 321 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1cb51836928943b2a630be9e28a61e28
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

Loading…