Sodium Carbonate → 2-{[(4-Fluorophenyl)methyl]oxy}-5-(1H-pyrazol-4-yl)-N-4-pyridazinylbenzamide

HRID 1623830Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12](C(OC(C)(C)C)=O)[CH:13]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:29]1[CH:30]=[CH:31][C:32]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)=[C:33]([CH:43]=1)[C:34]([NH:36][C:37]1[CH:42]=[CH:41][N:40]=[N:39][CH:38]=1)=[O:35]>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>[F:52][C:49]1[CH:48]=[CH:47][C:46]([CH2:45][O:44][C:32]2[CH:31]=[CH:30][C:29]([C:9]3[CH:13]=[N:12][NH:11][CH:10]=3)=[CH:43][C:33]=2[C:34]([NH:36][C:37]2[CH:42]=[CH:41][N:40]=[N:39][CH:38]=2)=[O:35])=[CH:51][CH:50]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1,1-Dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (110 mg, 0.37 mmol), sodium carbonate (0.75 ml, 0.75 mmol) and tetrakis(triphenylphosphine)palladium(0) (25.9 mg, 0.02 mmol) were added to a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-N-4-pyridazinylbenzamide (may be prepared as described in Example 77; 150 mg, 0.37 mmol) in 1,2-dimethoxyethane (5 ml). The reaction was heated at 120° C. for one hour. The solvent was removed in vacuo, triturated with 1:1 DMSO/methanol and washed with methanol (1 ml) and ethyl acetate (2 ml) to give a white solid. Recrystallisation with hot 1:1 DMSO/ethyl acetate yielded the title compound as a white solid. 48.6 mg.

Workup

customThe solvent was removed in vacuo
customtriturated with 1:1 DMSO/methanol
washwashed with methanol (1 ml) and ethyl acetate (2 ml)
customto give a white solid
customRecrystallisation with hot 1:1 DMSO/ethyl acetate

Sources & evidence

ORD record: ord-8ff71fd5affa4f76b398d5363ba75bf4
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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