Boron → 1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide

HRID 1625440Notes

Reaction equation

HRID 1625440 reaction equation
C(C1C=C2C(C3C=C(C=CC=3)CNC(C3C(=O)N(CC4C=CC(F)=C(F)C=4)C=CC=3)=O)=CNC2=NC=1)#N.[F:38][C:39]1[CH:40]=[C:41]([CH:63]=[CH:64][C:65]=1[F:66])[CH2:42][N:43]1[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([NH:51][CH2:52][C:53]2[CH:54]=[C:55](B(O)O)[CH:56]=[CH:57][CH:58]=2)=[O:50])[C:44]1=[O:62].[B].[Cl:68][C:69]1[CH:70]=[C:71]2[C:77](I)=[CH:76][NH:75][C:72]2=[N:73][CH:74]=1>>[Cl:68][C:69]1[CH:70]=[C:71]2[C:77]([C:55]3[CH:54]=[C:53]([CH:58]=[CH:57][CH:56]=3)[CH2:52][NH:51][C:49]([C:45]3[C:44](=[O:62])[N:43]([CH2:42][C:41]4[CH:63]=[CH:64][C:65]([F:66])=[C:39]([F:38])[CH:40]=4)[CH:48]=[CH:47][CH:46]=3)=[O:50])=[CH:76][NH:75][C:72]2=[N:73][CH:74]=1

Participants

5

Reactant 4

HCID 5462311BoronHCID 242292205-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridineHCID 59362353HCID 59362353, compoundHCID 593625581-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(5-cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide

Product 1

HCID 593625951-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide

Procedure

Except where indicated, 1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide was synthesized as per Example 68, 1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(5-cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide using 3-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-phenylboronic acid as activated boron species and 5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine as substituted bicyclic heterocycle, to yield the product. 1H NMR (300 MHz, CDCl3-MeOH-d4) d ppm 8.564 (dd, J=7.3, 2.2 Hz, 1H) 8.332 (d, J=2.0 Hz, 1H) 8.230 (d, J=2.1 Hz, 1H) 7.584 (s, 1H) 7.565 (s (br), 1H) 7.538 (dd, J=6.8, 2.1 Hz, 1H) 7.468-7.370 (m, 2H) 7.303 (d, J=6.9 Hz, 1H) 7.168-7.061 (m, 2H) 7.027-6.955 (m, 1H) 6.461 (t, J=6.9 Hz, 1H) 5.134 (s, 2H), 4.716-4.659 (m, 2); MS m/z=50.05 M+H.

Workup

  1. customto yield the product

Sources & evidence

ORD record
ord-2da028a17d334fd3acc193df40350209
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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