Formic Acid → HCID 178519611, compound

HRID 1898183Notes

Reaction equation

HRID 1898183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23](Cl)[N:22]=3)=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].C(O)=[O:33].O.C(=O)(O)[O-].[Na+]>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:33])[N:22]=3)=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:28]([F:29])([F:30])[F:31]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 57942290HCID 57942290, compound

Product 1

HCID 178519611HCID 178519611, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A 2 dram vial was charged with 4-chloro-N-[5-chloro-2-(6-chloro-pyridine-2-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (65 mg, 0.127 mmol), formic acid (2.0 mL) and water (0.50 mL). The heterogeneous solution was warmed to 110° C. and stirred overnight. The following day, the resultant mixture was neutralized with saturated aqueous sodium bicarbonate, diluted with EtOAc, and the organic layer washed with saturated sodium bicarbonate. The combined organics were dried with sodium sulfate, concentrated in vacuo, and purified via automated silica gel chromatography to afford the desired hydroxypyridine: MS (ES) (M+H)+ expected 492.0. found 491.9.

Workup

  1. washthe organic layer washed with saturated sodium bicarbonate
  2. dry with materialThe combined organics were dried with sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified

Sources & evidence

ORD record
ord-c0905388cbdf4588aab73595a72aa356
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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