Diethyl Ether → HCID 68739714, compound

HRID 2261255Notes

Reaction equation

HRID 2261255 reaction equation
B([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([F:14])[C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])(O)O.Br[C:16]1[C:21](=[O:22])[N:20]([CH3:23])[C:19]2[N:24]([C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[F:34])[N:25]=[CH:26][C:18]=2[CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].CCOCC>O1CCOCC1.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:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([F:34])[C:27]=1[N:24]1[C:19]2[N:20]([CH3:23])[C:21](=[O:22])[C:16]([C:4]3[CH:5]=[C:6]([CH:10]=[C:11]([F:14])[C:12]=3[CH3:13])[C:7]([OH:9])=[O:8])=[CH:17][C:18]=2[CH:26]=[N:25]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 46197691HCID 46197691, compoundHCID 671989493-Borono-5-fluoro-4-methylbenzoic acid

Product 1

HCID 68739714HCID 68739714, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

In a 25 mL sealed glass tube, a mixture of tetrakis(triphenylphosphine)palladium(0) (42 mg, 37 μmol), 3-borono-5-fluoro-4-methylbenzoic acid (218 mg, 1101 μmol), and 5-bromo-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (312 mg, 917 μmol) in 4.6 mL of dioxane and 1.0 M solution of sodium carbonate (2.3 mL, 2.3 mmol) was heated in a microwave at 130° C. for 30 min. The reaction mixture was treated with 15 mL of ether and washed with 5 mL of 2 N NaOH, The ether layer was discarded. The aqueous extracts were acidified to pH 4 with 5 N HCl and extracted with 3×25 mL EtOAc. The combined EtOAc layers were dried over MgSO4, filtered and concentrated in vacuo (rotovap) affording the title compound (296 mg) as a viscous oil which solidified to an off-white amorphous solid under vacuum overnight. MS (ESI, pos.ion) m/z: 414.0 (M+1).

Workup

  1. customIn a 25 mL sealed glass tube
  2. washwashed with 5 mL of 2 N NaOH
  3. extractionextracted with 3×25 mL EtOAc
  4. dry with materialThe combined EtOAc layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo (rotovap)

Sources & evidence

ORD record
ord-c30eef51e1054e8b834270e6907bf3f1
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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