Potassium Carbonate → HCID 59355006, compound

HRID 2196416Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].C([O-])([O-])=O.[K+].[K+].CC1(C)COB([C:25]2[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=2)OC1>O1CCOCC1.O.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:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[C:25]1[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=1)[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-bromo-3-fluorobenzoic acid (220 mg, 1.0 mmol) in dioxane/H2O (5:1, 12 mL) was added K2CO3 (414 mg, 3.0 mmol), tetrakistriphenylphosphine Pd(0) (58 mg, 0.05 mmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (214 mg, 1.1 mmol). The reaction mixture was heated to 80° C. in a sealed tube for 12 h and was then partitioned between 6N NaOH and DCM. The pH of the aqueous phase was adjusted to ˜3 with 3M HCl and washed several times with DCM. The combined organic fractions were dried (Na2SO4), concentrated under vacuum and used directly without further purification (196 mg, 89%): LC-MS (ES) m/z=221 (M+H)+.

Workup

customwas then partitioned between 6N NaOH and DCM
washwashed several times with DCM
dry with materialThe combined organic fractions were dried (Na2SO4)
concentrationconcentrated under vacuum
customused directly without further purification (196 mg, 89%)

Sources & evidence

ORD record: ord-51af3495baa94af2b4b8bd19352ad6e2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338434B2

Reaction notes

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