Sodium Carbonate → HCID 67387922, compound

HRID 905544Notes

Reaction equation

HRID 905544 reaction equation
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[O:14][CH:15]1[CH2:32][CH:31]2[N:17]([C:18](=[O:44])[N:19]([CH3:43])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH:26]3[C:28]([C:34]([NH:36][S:37]([CH:40]4[CH2:42][CH2:41]4)(=[O:39])=[O:38])=[O:35])([NH:29][C:30]2=[O:33])[CH2:27]3)[CH2:16]1.C[C:46]1[N:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1.[C:55](=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH3:55][C:48]1[CH:47]=[CH:46][N:51]=[CH:50][C:49]=1[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[O:14][CH:15]1[CH2:32][CH:31]2[N:17]([C:18](=[O:44])[N:19]([CH3:43])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH:26]3[C:28]([C:34]([NH:36][S:37]([CH:40]4[CH2:41][CH2:42]4)(=[O:39])=[O:38])=[O:35])([NH:29][C:30]2=[O:33])[CH2:27]3)[CH2:16]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 67388011HCID 67388011, compound

Product 1

HCID 67387922HCID 67387922, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 51 (17.3 mg, 0.025 mmol), 6-methylpyridine-3-boronic acid (5.9 mg, 0.028 mmol), tetrakistriphenylphosphine palladium (8.2 mg, 0.005 mmol) and sodium carbonate (5.8 mg, 0.055 mmol) in DMF (2 mL) were warmed to 90° C. for 20 h. Then, the reaction mixture was cooled down to room temperature and the solvent was evaporated. The residue was purified by HPLC to yield 3.7 mg (21%) of the title product 52 as a white powder. m/z=703 (M+H)+; 1H-NMR (CDCl3): 10.6 (bs, 1H), 8.8 (s, 1H), 8.12 (d, J=9.1 Hz, 1H), 7.97 (d, J=6.3 Hz, 1H), 7.9 (d, J=9.0 Hz, 1H), 7.54 (d, J=6.3 Hz, 1H), 7.3 (d, J=9.0 Hz, 1H), 7.21 (d, J=9.1 Hz, 1H), 6.68 (br s, 1H), 5.87 (br s, 1H), 5.74 (dd, J=17.3 Hz, 8.3 Hz, 1H), 5.16 (t, J=10.4 Hz, 1H), 4.74 (dd, J=9.4 Hz, 7.3 Hz, 1H), 4.11-3.98 (m, 4H), 3.69-3.55 (m, 2H), 3.27-3.10 (m, 1H), 3.02-2.89 (m, 1H), 2.83 (s, 3H), 2.58-2.35 (m, 3H), 2.50 (s, 3H), 2.29-2.13 (m, 1H), 2.11-1.92 (m, 2H), 0.75-1.76 (m, 9H).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-04b3bf3152d84f23839df6ecf01ecef2
Source dataset
uspto-grants-2011_09
Patent number
US08012939B2

Reaction notes

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