Hydrochloric Acid → HCID 71263608, compound

HRID 2272331Notes

Reaction equation

HRID 2272331 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:17]([C:22]2[C:40]([CH:41]3[CH2:43][CH2:42]3)=[CH:39][C:25]3[C:26]([C:36]([OH:38])=[O:37])=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[O:28][C:24]=3[CH:23]=2)[S:18]([CH3:21])(=[O:20])=[O:19])[CH:5]=[CH:6][C:7]=1[B:8]1[O:12]C(C)(C)C(C)(C)[O:9]1.I([O-])(=O)(=O)=O.[Na+].Cl.O>C1COCC1.CCOC(C)=O>[B:8]([C:7]1[CH:6]=[CH:5][C:4]([N:17]([C:22]2[C:40]([CH:41]3[CH2:42][CH2:43]3)=[CH:39][C:25]3[C:26]([C:36]([OH:38])=[O:37])=[C:27]([C:29]4[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=4)[O:28][C:24]=3[CH:23]=2)[S:18]([CH3:21])(=[O:20])=[O:19])=[CH:3][C:2]=1[Cl:1])([OH:9])[OH:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23667635Sodium periodateHCID 131732292HCID 131732292, compound

Product 1

HCID 71263608HCID 71263608, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-(N-(3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylic acid (110 mg, 0.171 mmol) and sodium periodate (183 mg, 0.856 mmol) in THF (14 mL) and aqueous 1N HCl (7 mL) was stirred at RT for 4 h then water and EtOAc were added. The organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by Reverse Phase HPLC (water/ACN+0.1% formic acid) to give 6-(N-(4-borono-3-chlorophenyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylic acid (24 mg, 0.041 mmol, 24% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.31 (br. s., 1H), 8.33 (s, 2H), 8.16 (s, 1H), 8.03 (d, 2H), 7.52-7.70 (m, 3H), 7.37-7.48 (m, 2H), 7.34 (dd, 1H), 3.40 (s, 3H), 2.09-2.22 (m, 1H), 0.64-1.11 (m, 3H), 0.47 (br. s., 1H). LCMS (m/z, ES+)=558.1 (M−H).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by Reverse Phase HPLC (water/ACN+0.1% formic acid)

Sources & evidence

ORD record
ord-1bea6dd1091940e5915d46595a436aa1
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

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