5-Bromo-2-methylpyridine → HCID 68408187, compound

HRID 888029Notes

Reaction equation

HRID 888029 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:33][C:34]1[CH:39]=[CH:38][C:37](Br)=[CH:36][N:35]=1>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20]([C:37]2[CH:36]=[N:35][C:34]([CH3:33])=[CH:39][CH:38]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 12010205-Bromo-2-methylpyridineHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 68408187HCID 68408187, compoundYield 46%

Procedure

Using an analogous procedure to that described in Method 4, N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Method 13, 1.20 g, 2.74 mmol) was reacted with 2-methyl-5-bromopyridine (505 mg, 2.94 mmol). The crude residue was purified by flash chromatography on silica (90 g), eluting with ethyl acetate/isohexane (40-100%) to give the title compound (504 mg, 46%); NMR Spectrum: (DMSO-d6) 1.46 (s, 9H), 2.51 (s, 3H), 7.19 (m, 2H), 7.40 (d, 1H), 7.58 (m, 2H), 7.91 (d, 2H), 8.08, (d, 3H), 8.66 (s, 1H), 8.86 (d, 1H), 9.89 (s, 1H); Mass Spectrum: M+H+ 404.

Workup

  1. customThe crude residue was purified by flash chromatography on silica (90 g)
  2. washeluting with ethyl acetate/isohexane (40-100%)

Sources & evidence

ORD record
ord-4e3496332f8c47f89a0749e8fb930873
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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