Methyl chloroformate → HCID 86706315, compound

HRID 2205925Notes

Reaction equation

HRID 2205925 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:10][C:4]=2[CH:3]=1.[CH3:17][O:18][C:19](Cl)=[O:20]>CN(C=O)C.C(OCC)(=O)C.O>[CH3:17][O:18][C:19]([N:10]1[C:4]2[CH:3]=[C:2]([Br:1])[N:7]=[CH:6][C:5]=2[CH:8]=[C:9]1[C:11]1[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=1)=[O:20]

Participants

6

Reactant 2

HCID 6586Methyl chloroformateHCID 867062766-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 86706315HCID 86706315, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 100 mg, 0.36 mmol) was dissolved in dry DMF (1 ml). The solution was degassed and a solution of sodium bis(trimethylsilyl)amide (0.55 ml of a 1M solution in THF, 0.55 mmol) was added. After 20 minutes reaction, methylchloroformate (52 mg, 0.55 mmol) was added and the reaction stirred for 2 hours at room temperature. The reaction was diluted with ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulphate and concentrated in vacuum. The crude product was purified on silica gel column chromatography eluting with 20% hexane in ethyl acetate followed by 2% methanol in ethyl acetate to afford the title compound as a white powder (95 mg, 79%). 1H NMR (500 MHz, CDCl3) 3.96 (s, 3H), 4 (s, 3H), 6.57 (s, 1H), 7.63 (s, 1H), 7.64 (s, 1H), 8.1 (s. 1H), 8.53 (s, 1H)

Workup

  1. customThe solution was degassed
  2. additiona solution of sodium bis(trimethylsilyl)amide (0.55 ml of a 1M solution in THF, 0.55 mmol) was added
  3. additionwas added
  4. washThe organic solution was washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuum
  7. customThe crude product was purified on silica gel column chromatography
  8. washeluting with 20% hexane in ethyl acetate

Sources & evidence

ORD record
ord-cbd639d5faca42f4876ef8aa2b4eed26
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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