Benzylamine → 5-(3-Fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid benzylamide

HRID 493152Notes

Reaction equation

HRID 493152 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Si](C)(C)[N:14]1[C:18]2=[N:19][CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:22]=[C:17]2[C:16]([C:30](O)=[O:31])=[CH:15]1)(C)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:1]([NH:8][C:30]([C:16]1[C:17]2[C:18](=[N:19][CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:22]=2)[NH:14][CH:15]=1)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 576811381-(tert-butyldimethylsilyl)-5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Product 1

HCID 101935515-(3-Fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid benzylamideYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzylamine (4.4 μL, 40.3 μmol) in dry CH2Cl2 (0.5 mL) was added carboxylic acid 10 (15 mg, 40.5 μmol), WSCHCl (9.32 mg, 44.86 μmol), HOBT (5.5 mg, 40.5 μmol) and i-Pr2NEt (7.1 μL, 40.8 μmol) and the reaction mixture left to stir at r.t. overnight Separation by LCMS (CombiPrep ODS-AM column) using water—acetonitrile as eluent (in gradient) afforded amide 11 (2.33 mg, 17%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 4.70 (d, J=5.5 Hz, 2H), 6.18 (t, J=5.5 Hz, 1H), 7.29-7.44 (m, 8H), 7.80 (s, 1H), 8.57 (d, J=1.8 Hz, 1H), 8.66 (d, J=2.1 Hz, 1H).

Workup

  1. waitthe reaction mixture left
  2. customSeparation by LCMS (CombiPrep ODS-AM column)

Sources & evidence

ORD record
ord-03a7b2e911414e729fd116dc2be53019
Source dataset
uspto-grants-2009_05
Patent number
US07534800B2

Reaction notes

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