Formic Acid → HCID 178519761, compound

HRID 1438583Notes

Reaction equation

HRID 1438583 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][N:24]=[C:23](Cl)[C:22]=3[Cl:28])=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].C(O)=[O:34].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][N:24]=[C:23]([OH:34])[C:22]=3[Cl:28])=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:29]([F:30])([F:31])[F:32]

Participants

6

Reactant 4

HCID 284Formic Acid2×HCID 962WaterHCID 516892Sodium BicarbonateHCID 57942107HCID 57942107, compound

Product 1

HCID 178519761HCID 178519761, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A 1 dram vial was charged with 4-chloro-N-[5-chloro-2-(2,3-dichloro-pyridine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (15 mg, 0.028 mmol), formic acid (0.39 mL) and water (0.13 mL). The heterogeneous solution was warmed to 100° C. and stirred overnight. The following day, starting material remained; therefore, an additional 0.26 mL of formic acid was added. The reaction was subsequently warmed to 110° C. and stirred overnight. 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: 1H NMR (400 MHz, CD3OD) δ 8.26-8.38 (m, 1 H), 8.17-8.20 (m, 2 H), 8.02-8.07 (m, 1 H), 7.72-7.76 (m, 1 H), 7.34-7.37 (m, 1 H), 6.17-6.20 (m, 1 H); MS (ES) (M+H)+ expected 525.9, found 525.9.

Workup

  1. temperatureThe reaction was subsequently warmed to 110° C.
  2. stirringstirred overnight
  3. washthe organic layer washed with saturated sodium bicarbonate
  4. dry with materialThe combined organics were dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified

Sources & evidence

ORD record
ord-5e0b8db5259649748fe9831c15318794
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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