Toluene → HCID 68892905, compound

HRID 2373306Notes

Reaction equation

HRID 2373306 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[N:13][C:12]([CH3:15])=[C:11]3[O:16][C:17]([CH3:21])([CH3:20])[O:18][CH2:19][C:10]=23)=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:28]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1B(O)O)(=[O:35])=[O:34])([CH3:31])([CH3:30])[CH3:29].C1(C)C=CC=CC=1>O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C(C)C>[C:28]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:2]1[CH:7]=[N:6][C:5]([NH:8][C:9]2[CH:14]=[N:13][C:12]([CH3:15])=[C:11]3[O:16][C:17]([CH3:21])([CH3:20])[O:18][CH2:19][C:10]=23)=[CH:4][CH:3]=1)(=[O:35])=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 69099857HCID 69099857, compound

Product 1

HCID 68892905HCID 68892905, compoundYield 74.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 6560IsobutanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (5-bromo-pyridin-2-yl)-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-amine (10) (564 mg, 1.55 mmol), tetrakis(triphenylphosphine) palladium(0) (174 mg, 0.15 mmol), cesium carbonate (1.56 g, 4.8 mmol), 2-tert-butylsulfamoyl-phenylboronic acid (438 mg, 1.7 mmol) in a solution of toluene (20 mL), iso-butyl alcohol (15 mL) and water (5 mL) was stirred at 80° C. under nitrogen for 5 h. The reaction was diluted with water and extracted with ethyl ether. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated. The crude product was purified by column chromatography on silica gel to give N-tert-butyl-2-[6-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylamino)-pyridin-3-yl]-benzenesulfonamide (11) as a colorless solid (554 mg, 74% yield).

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e707808ccb2d470e923648e80e04b3bb
Source dataset
uspto-grants-2008_12
Patent number
US07459468B2

Reaction notes

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