Sodium Bicarbonate → HCID 11188919, compound

HRID 2353394Notes

Reaction equation

HRID 2353394 reaction equation
Br[C:2]1[C:16]([F:17])=[CH:15][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28](B(O)O)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1.C(=O)([O-])O.[Na+]>C(O)(C)C.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>[CH:18]1([NH:21][C:22](=[O:23])[C:24]2[CH:29]=[C:28]([C:2]3[C:16]([F:17])=[CH:15][C:5]4[C:6]([C:9]5[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=5)=[N:7][O:8][C:4]=4[CH:3]=3)[C:27]([CH3:33])=[C:26]([F:34])[CH:25]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21914527(5-(Cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)boronic acidHCID 58830628HCID 58830628, compound2×

Product 1

HCID 11188919HCID 11188919, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

The procedure for Example 1 was followed using 6-bromo-5-fluoro-3-(4-pyridinyl)-1,2-benzisoxazole (Intermediate 6, 25 mg), {5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}boronic acid (24 mg), tetrakis(triphenylphosphine)palladium(0) (1 mg) and saturated aqueous sodium hydrogen carbonate (0.25 ml) in isopropanol (1 ml). Elution of the SPE cartridge (silica, 1 g) with cyclohexane/ethyl acetate (100:0 to 66:33) gave the title compound as a white solid (21 mg).

Workup

  1. washElution of the SPE cartridge (silica, 1 g) with cyclohexane/ethyl acetate (100:0 to 66:33)

Sources & evidence

ORD record
ord-7e27d730632b468c80b21053b9769d47
Source dataset
uspto-grants-2010_07
Patent number
US07750026B2

Reaction notes

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