Sodium Carbonate → HCID 58784945, compound

HRID 1375058Notes

Reaction equation

HRID 1375058 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5](Cl)[S:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.[Cl-].[Na+].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>[NH2:1][C:2]1[CH:6]=[C:5]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[S:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 109559343-Amino-5-chlorothiophene-2-sulfonamide

Product 1

HCID 58784945HCID 58784945, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3b (104 mg, 0.5 mmol) in 1,4-dioxane/water (40 mL, 3:1) was added 4-fluorophenylboronic acid (140 mg, 1 mmol), Na2CO3 (212 mg, 2 mmol), and Pd(PPh3)4 (9% Pd, 59 mg, 0.05 mmoL). The resultant mixture was heated at 110° C. for 3 h, diluted with brine solution (50 mL) and extracted with ethyl acetate (50 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 1:1) then provided 3c (45 mg, 33%) as a yellow solid: MS (ES) 273 (M+H)+; 1H NMR (400 MHz, MeOD) δ7.52 (m, 2 H), 7.04 (m, 2 H), 6.72 (s, 1 H).

Workup

  1. extractionextracted with ethyl acetate (50 mL, 3×)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-880bfabf377d4a53a71c2744e45fd4a7
Source dataset
uspto-grants-2007_01
Patent number
US07166639B2

Reaction notes

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