4-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester → 4-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid

HRID 593525Notes

Reaction equation

HRID 593525 reaction equation
C([O:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([C:24]#[N:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:14])=[CH:9][CH:8]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[C:24]([C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[N:15]([C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:6]([OH:32])=[O:5])=[CH:12][CH:11]=1)=[O:14])[C:16]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[CH:17]2)#[N:25]

Participants

3

Reactant 1

HCID 582157224-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester

Product 1

HCID 582157044-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester (100 mg) is dissolved in TFA (3 mL) and stirred at ambient temperature for 1 h. The solvent is removed in vacuo and the residue is triturated with diethyl ether twice. The residue is purified by reverse phase HPLC with Sunfire C18 and a gradient of acetonitrile in 0.1% aqueous TFA to afford 4-(5-cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm (TFA salt) 7.24 (s, 1H), 7.28 (dd, J=7.9, 4.9 Hz, 1H), 7.73-7.77 (m, 4H), 7.81 (dt, J=8.1, 1.9, 1.8 Hz, 1H), 7.87-7.91 (m, 2H), 8.32 (t, J=1.1 Hz, 1H), 8.41 (dd, J=4.9, 1.6 Hz, 1H), 8.63-8.65 (m, 1H), 13.40 (br. s., 1H). HRMS (ESI) m/z 366.0868 [(M+H)+ Calcd for C22H14N3O3: 366.0879].

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is triturated with diethyl ether twice
  3. customThe residue is purified by reverse phase HPLC with Sunfire C18

Sources & evidence

ORD record
ord-552743c060df4baab0169f739e47a684
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

Loading…