Methyl chloroformate → HCID 59161300, compound

HRID 545564Notes

Reaction equation

HRID 545564 reaction equation
[NH2:1][CH:2]1[CH2:14][CH2:13][C:12]2[NH:11][C:10]3[CH:9]=[CH:8][C:7]([C:15]#[N:16])=[CH:6][C:5]=3[C:4]=2[CH2:3]1.C(N(CC)CC)C.Cl[C:25]([O:27][CH3:28])=[O:26]>CS(C)=O>[CH3:28][O:27][C:25](=[O:26])[NH:1][C@H:2]1[CH2:3][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[C:7]([C:15]#[N:16])[CH:6]=3)[NH:11][C:12]=2[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 9837225HCID 9837225, compound

Product 1

HCID 59161300HCID 59161300, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 6-amino-6,7,8,9-tetrahydro-5H-carbazole-3-carbonitrile (2.4 mmol, 0.5 g) and triethylamine (4.7 mmol, 0.66 mL) in DMSO (10 mL) with 15 stirring. Add methyl chloroformate (3.6 mmol, 275 μL) and stir the resulting mixture at room temperature for 5-10 min. Quench with water (35 mL) and dilute the reaction mixture with ethyl acetate (200 mL). Separate the layers and wash the organic layer with with brine (100 mL). Back wash the brine layer with ethyl acetate (2×100 mL) and dry the combined organic layers with magnesium sulfate. Filter and concentrate in vacuo to provide crude product that is used without further purification. LCMS of the reaction mixture prior to workup gave masses 270.0 (APCI-pos) and 268.0 (APCI-neg) for the desired product.

Workup

  1. customQuench with water (35 mL)
  2. additiondilute the reaction mixture with ethyl acetate (200 mL)
  3. customSeparate the layers
  4. washwash the organic layer with with brine (100 mL)
  5. washBack wash the brine layer with ethyl acetate (2×100 mL)
  6. dry with materialdry the combined organic layers with magnesium sulfate
  7. filtrationFilter
  8. concentrationconcentrate in vacuo
  9. customto provide crude product that
  10. customis used without further purification

Sources & evidence

ORD record
ord-29811aad7092445b8e21c8eb25cd342a
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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