Acetyl chloride → HCID 59741014, compound

HRID 2192156Notes

Reaction equation

HRID 2192156 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]2[NH:17][CH:18]=[CH:19][C:12]=12)[NH2:6].C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28].C(=O)(O)[O-].[Na+].C[O-].[Na+]>ClCCl>[F:2][C:3]1[CH:4]=[C:5]([NH:6][C:27](=[O:29])[CH3:28])[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]2[NH:17][CH:18]=[CH:19][C:12]=12

Participants

7

Reactant 5

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 69309881HCID 69309881, compound

Product 1

HCID 59741014HCID 59741014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.00 g (17.9 mmol) of 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline hydrochloride are suspended in 100 ml of dichloromethane and cooled to 0° C. 9.97 ml (71.5 mmol) of triethylamine and 3.81 ml (53.6 mmol) of acetyl chloride are added dropwise, and the mixture is stirred at 0° C. for another 2 hours. Saturated sodium bicarbonate solution is added, and the mixture is stirred at RT for 10 min. The mixture is then extracted twice with dichloromethane. Insoluble components are dissolved using a little acetone, and the mixture is diluted with dichloromethane and washed with saturated sodium chloride solution. The combined organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure. The crude product is taken up in 100 ml of ethanol. 3.31 ml (17.9 mmol) of 5.4 M sodium methoxide solution are added, and the mixture is stirred at RT for 30 min. The mixture is concentrated and the product is purified by chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 100:5).

Workup

  1. stirringthe mixture is stirred at RT for 10 min
  2. extractionThe mixture is then extracted twice with dichloromethane
  3. dissolutionInsoluble components are dissolved
  4. additionthe mixture is diluted with dichloromethane
  5. washwashed with saturated sodium chloride solution
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. customthe solvent is removed under reduced pressure
  8. stirringthe mixture is stirred at RT for 30 min
  9. concentrationThe mixture is concentrated
  10. customthe product is purified by chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 100:5)

Sources & evidence

ORD record
ord-5ce0ba9dfcf04f769bef72109031babb
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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