Sodium Carbonate → HCID 66611992, compound

HRID 2204730Notes

Reaction equation

HRID 2204730 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[C:9]([CH2:31][N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:10][C:11]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:12]([CH:22]=1)[C:13]([NH:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:14].[CH3:38][N:39]1[CH:43]=[C:42](B(O)O)[CH:41]=[N:40]1>COCCOC.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>[CH3:38][N:39]1[CH:43]=[C:42]([C:8]2[C:9]([CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:10][C:11]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:12]([CH:22]=2)[C:13]([NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:14])[CH:41]=[N:40]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 112635011-Methyl-1H-pyrazole-4-boronic acidHCID 66612041HCID 66612041, compound

Product 1

HCID 66611992HCID 66611992, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

Na2CO3 (0.23 ml, 0.23 mmol) and palladium tetrakis (7.91 mg, 6.84 μmol) were added to 5-bromo-4-(4-morpholinylmethyl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 2; 55 mg, 0.11 mmol) and (1-methyl-1H-pyrazol-4-yl)boronic acid (17.23 mg, 0.137 mmol) in 1,2-dimethoxyethane (3 ml). The mixture was heated at 120° C. in a microwave for one hour and the solvent was removed in vacuo. The residue was purified by MDAP to yield the title compound as a white solid. 27 mg.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-a2661b655755422cbdf1a3318b634a79
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

Loading…