Sodium Carbonate → HCID 59970507, compound

HRID 380025Notes

Reaction equation

HRID 380025 reaction equation
[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:24]1[CH:39]=[CH:38][C:27]([C:28]([NH:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)=[O:29])=[CH:26][C:25]=1[CH3:40].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:33]1([CH2:32][CH2:31][NH:30][C:28]([C:27]2[CH:38]=[CH:39][C:24]([C:8]3[CH:9]=[CH:10][C:5]([O:4][C@@H:3]([CH3:14])[C@H:2]([OH:1])[CH2:15][CH2:16][C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)=[CH:6][CH:7]=3)=[C:25]([CH3:40])[CH:26]=2)=[O:29])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 18367611HCID 18367611, compoundHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Product 1

HCID 59970507HCID 59970507, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.15 g, Example 33), 4-bromo-3-methyl-N-(2-pyrrolidin-1-yl-ethyl)benzamide (0.31 g, Example 63a)), 2M aqueous sodium carbonate (0.57 ml) and tetrakis(triphenylphosphine)palladium(0) (0.012 g) in ethanol(5 ml) with heating at reflux for 4 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-10% ethanol in dichloromethane to give the title compound as an oil. (0.14 g).

Workup

  1. customPrepared
  2. temperaturewith heating
  3. temperatureat reflux for 4 hours
  4. customAfter work up, the residue was purified by normal-phase HPLC
  5. washeluting with a gradient of 0-10% ethanol in dichloromethane

Sources & evidence

ORD record
ord-b3d0ad9bf53543b2bddebb1ddad516d9
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

Loading…