Bromide ion → HCID 59362846, compound

HRID 1625457Notes

Reaction equation

HRID 1625457 reaction equation
S1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]2[C:14]([C:15]3[CH:16]=[C:17]([CH:38]=[CH:39][CH:40]=3)[CH2:18][NH:19][C:20]([C:22]3[C:23](=[O:37])[N:24]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=4)[CH:25]=[CH:26][CH:27]=3)=[O:21])=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1.BrC1[O:43]C=CC=1.[Br-]>[Pd]>[O:43]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]2[C:14]([C:15]3[CH:16]=[C:17]([CH:38]=[CH:39][CH:40]=3)[CH2:18][NH:19][C:20]([C:22]3[C:23](=[O:37])[N:24]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=4)[CH:25]=[CH:26][CH:27]=3)=[O:21])=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 2776190Furan, 2-bromo-HCID 59362582HCID 59362582, compound

Product 1

HCID 59362846HCID 59362846, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

Except where indicated, 1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(5-furan-2-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide was synthesized as per Example 95, 1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(5-thiophen-2-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide using 2-Bromo-furan as bromide in the second palladium coupling, to yield the product. 1H NMR (400 MHz, CDCl3-MeOH-d4) ppm 10.237 (m, 1H) 8.813 (s, 1H) 8.594 (s, 1H) 8.510 (d, J=7.0 Hz, 1H) 7.669 (s, 1H) 7.587 (s, 1H) 7.543 (d, J=6.1 Hz, 1H) 7.508 (s, 1H) 7.490-7.391 (m, 2H) 7.346 (d, J=6.7 Hz, 1H) 7.132-7.014 (m, 2H) 6.991-6.925 (m, 1H) 6.868 (d, J=2.9 Hz, 1H) 6.495 (m, 1H) 6.440 (t, J=6.7 Hz, 1H) 5.079 (s, 2H) 4.677 (m, 2H); MS m/z=537.31 M+H.

Workup

  1. customto yield the product

Sources & evidence

ORD record
ord-1e2fb96214d748be9821a2c743bc6e54
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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