Sodium Carbonate → HCID 66614654, compound

HRID 2204735Notes

Reaction equation

HRID 2204735 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[C:22]([CH3:23])=[CH:21][C:11]([C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[C:10]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:9]=1.[CH3:32][N:33]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[N:34]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>[CH3:23][C:22]1[C:8]([C:36]2[CH:35]=[N:34][N:33]([CH3:32])[CH:37]=2)=[CH:9][C:10]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:11]([CH:21]=1)[C:12]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 66611955HCID 66611955, compound

Product 1

HCID 66614654HCID 66614654, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

Sodium carbonate (0.30 ml, 0.30 mmol) was added to 4-bromo-5-methyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 9; 59 mg, 0.15 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (37.1 mg, 0.18 mmol) and palladium tetrakis (10.30 mg, 8.91 μmol) in 1,2-dimethoxyethane (3 ml). The mixture was heated in a microwave at 120° C. for 1 hour, the solvent was removed in vacuo and the solid purified by MDAP to yield the title compound as a white solid. 30 mg.

Workup

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

Sources & evidence

ORD record
ord-577ebc7045c243e4b89f16c1ca2ba4fd
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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