Sodium Carbonate → HCID 69936922, compound

HRID 1623813Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.C([O-])([O-])=O.[Na+].[Na+].Br[C:23]1[CH:24]=[CH:25][C:26]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:27]([CH:37]=1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][N:34]=[N:33][CH:32]=1)=[O:29].CS(C)=O.CO>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>[CH3:1][N:2]1[CH:6]=[C:5]([C:23]2[CH:24]=[CH:25][C:26]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:27]([CH:37]=2)[C:28]([NH:30][C:31]2[CH:36]=[CH:35][N:34]=[N:33][CH:32]=2)=[O:29])[CH:4]=[N:3]1

Participants

Conditions

Temperature: 140 °C

Procedure

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (56.9 mg, 0.273 mmol), 1M Na2CO3 (0.52 ml, 0.52 mmol) and tetrakis(triphenylphosphine)palladium(0) (18 mg, 6 mol %) were added to a solution of 5-bromo-2-[(phenylmethyl)oxy]-N-4-pyridazinylbenzamide (may be prepared as described in Example 6; 100 mg, 0.26 mmol) in 1,2-dimethoxyethane (3 ml). The solution was heated at 140° C. in microwave for 35 minutes. The solvent was removed in vacuo to give a residue. Trituration with 1:1 dimethyl sulfoxide/methanol (0.6 ml) gave the product as a solid which was washed with methanol (2 ml) and ethyl acetate (5 ml) to yield the title compound as a grey solid. 45 mg.

Workup

customThe solvent was removed in vacuo
customto give a residue

Sources & evidence

ORD record: ord-e607b5a75db649e78556cff39a15b212
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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