Sodium Carbonate → HCID 66611948, compound

HRID 2204736Notes

Reaction equation

HRID 2204736 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:20]=[CH:19][N:18]=[N:17][CH:16]=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:20]=[CH:19][N:18]=[N:17][CH:16]=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 666115484-Bromo-5-methyl-2-[(phenylmethyl)oxy]-N-4-pyridazinylbenzamide

Product 1

HCID 66611948HCID 66611948, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

Sodium carbonate (0.32 ml, 0.32 mmol) was added to 4-bromo-5-methyl-2-[(phenylmethyl)oxy]-N-4-pyridazinylbenzamide (may be prepared as described in Example 10; 64 mg, 0.16 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (40.1 mg, 0.19 mmol) and Pd(Ph3P)4 (11.14 mg, 9.64 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 triturated with DMSO/methanol (1:1, 1 ml) to yield the title compound as a white solid. 9 mg.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe solid triturated with DMSO/methanol (1:1, 1 ml)

Sources & evidence

ORD record
ord-e60ce028a9c64327b6742b4ea54f9abd
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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