Sodium Carbonate → HCID 58726831, compound

HRID 502580Notes

Reaction equation

HRID 502580 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:31]=[CH:30][C:12]2[C:13]([NH:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=3)=[N:14][S:15][C:11]=2[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([NH:5][S:6]([C:9]1[CH:31]=[CH:30][C:12]2[C:13]([NH:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([C:22]3[CH:27]=[CH:26][C:25]([C:37]4[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=4)=[CH:24][CH:23]=3)=[O:29])=[N:14][S:15][C:11]=2[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 57436518HCID 57436518, compound

Product 1

HCID 58726831HCID 58726831, compoundYield 34.2%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(3-(6-(N-tert-butylsulfamoyl)benzo[d]isothiazol-3-ylamino)propyl)4-iodobenzamide (50 mg, 0.09 mmol), 4-methoxyphenylboronic acid (14 mg, 0.09 mmol), tetrabutylammonium bromide (29 mg, 0.09 mmol), sodium carbonate (29 mg, 0.27 mmol) and palladium (II) acetate (1 mg) in water (3 mL) was microwaved at 160° C. for 5 min. The reaction was diluted with methylene chloride and the mixture was washed successively with aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography, on silica gel, eluting with 98:2 methylene chloride:methanol yielded N-(3-(6-(N-tert-butylsulfamoyl)benzo[d]isothiazol-3-ylamino)propyl)-4′-methoxybiphenyl-4-carboxamide (17 mg), as a white solid. 1H NMR (300 MHz, DMSO-d6): 8.70 (s, 1H), 8.52 (t, 1H), 8.10 (d, 1H), 7.86 (d, 2H), 7.81 (t, 1H), 7.68 (t, 3H), 7.52-7.60 (m, 2H), 6.97-7.08 (m, 2H), 3.80 (s, 3H), 3.49-3.57 (m, 4H), 1.95 (t, 2H), 1.12 ppm (s, 9H). MW=553 confirmed by LC-MS, tr=4.30 min (Method B) MH+=554.

Workup

  1. customwas microwaved at 160° C. for 5 min
  2. washthe mixture was washed successively with aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography
  7. washon silica gel, eluting with 98:2 methylene chloride

Sources & evidence

ORD record
ord-15eb32eb97864eedb5e70e1d62579388
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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