4-Fluorobenzyl bromide → 1-(4-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 2221471Notes

Reaction equation

HRID 2221471 reaction equation
FC1C=CC(CN2C3=CN=C(C(OCC)=O)C=C3C=C2)=CC=1.N1C2=CN=C(C(OCC)=O)C=C2C=C1.FC1C=CC(CBr)=CC=1.FC1C=C(F)C=CC=1CN1C2=CN=C(C(O)=O)C=C2C=C1.F[C:68]1[CH:87]=[C:86]([F:88])[CH:85]=[CH:84][C:69]=1[CH2:70][N:71]1[C:75]2=[CH:76][N:77]=[C:78]([C:80]([NH:82][OH:83])=[O:81])[CH:79]=[C:74]2[CH:73]=[CH:72]1.FC1C=CC(CN2C3=CN=C(C(O)=O)C=C3C=C2)=CC=1.Cl.NO>>[F:88][C:86]1[CH:87]=[CH:68][C:69]([CH2:70][N:71]2[C:75]3=[CH:76][N:77]=[C:78]([C:80]([NH:82][OH:83])=[O:81])[CH:79]=[C:74]3[CH:73]=[CH:72]2)=[CH:84][CH:85]=1

Participants

8

Reactant 7

HCID 680214-Fluorobenzyl bromideHCID 443297Hydroxyamine hydrochlorideHCID 99483631-[(2,4-Difluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acidHCID 10702827ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylateHCID 21892199Ethyl 1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate2×HCID 218922071-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acidHCID 218922121-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid

Product 1

HCID 100624691-(4-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

Procedure

Ethyl 1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate. The title compound was prepared by alkylation of ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylate with 4-fluorobenzyl bromide in a manner similar to step (a) of example 1. 1H NMR (CD3OD) δ: 8.91 (s, 1H), 8.62 (s, 1H), 7.90 (d, 1H, J=3.0 Hz), 7.42 (m, 2H), 7.20 (m, 2H), 6.90 (d, 1H, J=3.0 Hz), 5.75 (s, 2H), 4.60 (q, 2H, J=7.0 Hz), 1.60 (t, 3H, J=7.0 Hz). LCMS (API-ES, M+H+): 299.1. (b) 1-(4-Fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate in a manner similar to step (b) of example 1. 1H NMR (DMSO-d6): δ: 8.97 (s, 1H), 8.35 (s, 1H), 7.90 (d, 1H, J=3.0 Hz), 7.35 (m, 2 H), 7.15 (m, 2H), 6.76 (d, 1H, J=3.0 Hz), 5.67 (s, 2H). LCMS (API-ES, M+H+): 271.1. (c) 1-(4-Fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide. The title compound was prepared by coupling of 1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid with hydroxylamine hydrochloride in a manner similar to step (c) of example 1. 1H NMR (DMSO-d6) δ: 11.12 (s, 1H), 8.90 (s, 1H), 8.83 (s, 1H), 8.21 (s, 1H), 7.85 (d, 1H, J=3 Hz), 7.36 (d, 2H, J=8.3 Hz), 7.17 (d, 2H, J=8.4 Hz), 6.71 (d, 1H, J=3.0 Hz), 5.59 (s, 2H). LCMS (API-ES, M+H+): 286.1. HRMS calcd for C15H13FN3O2 (M+H) 286.0992, found 286.0978. Anal. (C15H12FN3O2) C, H, N. HPLC: 96.6% purity.

Sources & evidence

ORD record
ord-4a9a547db48f48b4899870fd10663392
Source dataset
uspto-grants-2008_05
Patent number
US07368571B2

Reaction notes

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