Water → HCID 118275229, compound

HRID 526009Notes

Reaction equation

HRID 526009 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9]([C:11](=[O:28])[NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:17])([F:16])[F:15])=[CH:10][C:5]2=[CH:4][C:3]=1[C:29]([O:31][CH3:32])=[O:30].[H-].[Na+].I[CH2:36][CH3:37].O>CN(C)C=O.C(OCC)(=O)C>[CH2:36]([N:8]1[C:6]2=[N:7][C:2]([CH3:1])=[C:3]([C:29]([O:31][CH3:32])=[O:30])[CH:4]=[C:5]2[CH:10]=[C:9]1[C:11](=[O:28])[NH:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)[C:14]([F:15])([F:16])[F:17])[CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 90039588HCID 90039588, compound

Product 1

HCID 118275229HCID 118275229, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.58 g, 3.44 mmol) was dissolved under argon at 0° C. in N,N-dimethylformamide (35 ml). Sodium hydride (60%; 0.165 g, 4.12 mmol) was added and the mixture was stirred with ice cooling for 2 h. Iodoethane (0.643 g, 4.12 mmol) was added and the reaction mixture was thawed with stirring over 18 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was removed under reduced pressure. The residue was chromatographed with cyclohexane/ethyl acetate (3/1) and gave 1.15 g (66% of theory) of methyl 1-ethyl-6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate. HPLC-MS: log P=6.27; mass (m/z): 488.1 (M+H)+; 1HNMR (D6-DMSO): δ 1.20 (t, 3H), 2.83 (s, 3H), 3.87 (s, 3H), 4.59 (q, 2H), 6.30-6.34 (m, 1H), 7.42 (s, 1H), 7.70-7.84 (m, 2H), 8.06 (d, 1H), 7.93-7.97 (m, 1H), 8.21 (s, 1H), 8.67 (s, 1H).

Workup

  1. stirringwith stirring over 18 h
  2. customthe phases were separated
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed with cyclohexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-c8a7ec36a09e4bb1ac12e657ac241002
Source dataset
uspto-grants-2016_05
Patent number
US09345247B2

Reaction notes

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