Potassium Carbonate → HCID 66707449, compound

HRID 1500403Notes

Reaction equation

[C:1]([O:5][C:6](=[O:26])[CH2:7][C:8]1[C:9]([CH2:24][CH3:25])=[N:10][N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][C:17]=2[F:23])[C:12]=1[CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].O1CCOCC1.C(N(C(C)C)CC)(C)C.[C:42](=O)([O-:44])[O-:43].[K+].[K+]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].O>[C:1]([O:5][C:6]([CH2:7][C:8]1[C:9]([CH2:24][CH3:25])=[N:10][N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:42]([OH:44])=[O:43])=[CH:18][C:17]=2[F:23])[C:12]=1[CH2:13][CH3:14])=[O:26])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

To a microwave vial was added [1-(4-bromo-2-fluorobenzyl)-3,5-diethyl-1H-pyrazol-4-yl]acetic acid tert.-butyl ester (6.5 g), dioxane (30 ml), water (15 ml), molybdenum hexacarbonyl (2.1 g), Hermann's catalyst (1.5 g) and diisopropylethylamine (6 ml). After 20 min microwave heating at 150° C., the vial is allowed to cool to room temperature and the content is added to water. The reaction mixture is made alkaline with potassium carbonate and extracted twice with ethyl acetate. The aqueous phase is separated, acidified with glacial acetic acid and extracted several times with dichloromethane. The organic phase is then separated, dried over magnesium sulfate and concentrated in vacuo to yield 4-(4-tert.-butoxycarbonylmethyl-3,5-diethylpyrazol-1-ylmethyl)-3-fluorobenzoic acid (3.4 g; [M+H]=391; HPLC retention time 1.00 min (Method K)).

Workup

temperatureto cool to room temperature
extractionextracted twice with ethyl acetate
customThe aqueous phase is separated
extractionextracted several times with dichloromethane
customThe organic phase is then separated
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-12a1647a3e31435b9764aa07d8c00952
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206164B2

Reaction notes

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