Trifluoroacetic acid → benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

HRID 875402Notes

Reaction equation

HRID 875402 reaction equation
FC(F)(F)C(O)=O.CC([NH:16][C:17]1[C:22]2[CH:23]=[CH:24][N:25]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[C:21]=2[CH:20]=[CH:19][N:18]=1)(CC(C)(C)C)C>ClCCl>[NH2:16][C:17]1[C:22]2[CH:23]=[CH:24][N:25]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[C:21]=2[CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71061424benzyl 4-[(2,4,4-trimethylpentan-2-yl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 71061834benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added drop wise to an ice-cooled suspension of benzyl 4-[(2,4,4-trimethylpentan-2-yl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (5 g, 9.7 mmol, Step c) in dichloromethane (30 mL). The reaction mixture was stirred at room temperature for 4 hours. Upon completion, the reaction mixture was concentrated under vacuum and the residue was stirred in excess aqueous ammonia solution. The precipitated solid was filtered under suction, washed with water and dried to yield benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.5 g, 95%) as off-white solid.

Workup

  1. temperaturecooled
  2. concentrationUpon completion, the reaction mixture was concentrated under vacuum
  3. stirringthe residue was stirred in excess aqueous ammonia solution
  4. filtrationThe precipitated solid was filtered under suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-427b290fe4f64d818ce45594346bfbdf
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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