Formic Acid → HCID 64992061, compound

HRID 1526281Notes

Reaction equation

HRID 1526281 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Br:11][C:12]1[N:17]=[C:16]([NH2:18])[CH:15]=[CH:14][CH:13]=1>O1CCCC1>[Br:11][C:12]1[N:17]=[C:16]([NH:18][CH:5]=[O:7])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 64992061HCID 64992061, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

To acetic anhydride (1.5 mL) was added dropwise formic acid (0.73 mL) under ice-cooling, and the mixture was stirred at 55° C. for 45 min. The mixture was allowed to be warmed to room temperature, tetrahydrofuran (20 mL) was added thereto, and a solution of 6-bromopyridin-2-amine (1.00 g) in tetrahydrofuran (10 mL) was added dropwise thereto over 3 min under ice-cooling. The reaction mixture was stirred at room temperature for 1.5 hr. The reaction solution was concentrated under reduced pressure, and the obtained white solid was subjected to azeotropy with toluene, and washed with hexane to give the title compound (1.1 g).

Workup

  1. temperaturecooling
  2. temperatureto be warmed to room temperature
  3. temperatureover 3 min under ice-cooling
  4. stirringThe reaction mixture was stirred at room temperature for 1.5 hr
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. washwashed with hexane

Sources & evidence

ORD record
ord-279ffad743f6433b83ea827e8eae3986
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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