Sodium Carbonate → HCID 67231791, compound

HRID 1511993Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:8]2[CH:23]=[C:24](Br)[CH:25]=[C:7]2[C:6]=1[OH:27])=[O:4].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(N(C)C)=O.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:8]2[CH:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:25]=[C:7]2[C:6]=1[OH:27])=[O:4]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-bromo-4-hydroxy-2-oxo-1-(4-trifluoromethyl-benzyl)-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid methyl ester (446 mg), phenyl boronic acid (366 mg), PEPPSI-IPr (34 mg; Total Synthesis Ltd./Sigma-Aldrich), and sodium carbonate solution (1.0 mL, 2 M in water) in DMA (10 mL) was heated at 120° C. for 5 h; the mixture was then cooled, diluted with EtOAc, washed with water, diluted HCl solution and sat. NaCl solution respectively; subsequently, the organic phase was dried over sodium sulfate, filtered, concentrated, and the residue was column purified (eluent: DCM/MeOH) to give the desired product (59 mg). ESI (m/z): 443 (M+H)+.

Workup

temperaturethe mixture was then cooled
washwashed with water, diluted HCl solution and sat. NaCl solution respectively
dry with materialsubsequently, the organic phase was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified (eluent: DCM/MeOH)

Sources & evidence

ORD record: ord-98eae8bd18b343a3ba8eb2dc3e2d861d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217043B2

Reaction notes

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