Sodium Carbonate → HCID 59726009, compound

HRID 422544Notes

Reaction equation

HRID 422544 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.Br[C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33]([O:37][CH2:38][C:39]([F:42])([F:41])[F:40])=[N:32][N:31]=[CH:30]2.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>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>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33]([O:37][CH2:38][C:39]([F:41])([F:42])[F:40])=[N:32][N:31]=[CH:30]2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 59261368HCID 59261368, compoundHCID 59726030HCID 59726030, compound

Product 1

HCID 59726009HCID 59726009, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-methyl-N-(1-methyl-1H-pyrazol-5-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (19, 143 mg, 0.42 mmol), 6-bromo-1-(2,2,2-trifluoroethoxy)phthalazine (20, 117 mg, 0.38 mmol), tetrakis(triphenylphosphine)palladium (22.0 mg, 0.019 mmol) in 2 mL of Dioxane and 0.5 mL of 2 N aqueous solution of Na2CO3 in a sealed glass tube was heated at 120° C. for 20 min in a Personal Chemistry microwave. The mixture was treated with 3 mL of 1 N NaOH and extracted with EtOAc (2×10 mL). The combined EtOAc layers were dried and concentrated. Purification of the residue on a 24 g ISCO column (eluted 75-100% EtOAc in Hexanes) provided the title compound 21 as an off-white solid. MS (ESI, pos. ion) m/z: 442.1 (M+1).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. dry with materialThe combined EtOAc layers were dried
  3. concentrationconcentrated
  4. customPurification of the residue
  5. washon a 24 g ISCO column (eluted 75-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-e8f9c70aa3f64ff2a18152581f92aaa3
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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