Methyl iodide → HCID 68283765, compound

HRID 1527223Notes

Reaction equation

HRID 1527223 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18](=[O:20])[NH2:19])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[C:22]([O-])([O-])=O.[Cs+].[Cs+].CI>CS(C)=O>[C:1]([O:5][C:6](=[O:21])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:22])=[CH:14][CH:15]=2)[C:10]([C:18](=[O:20])[NH2:19])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 68283907HCID 68283907, compound

Product 1

HCID 68283765HCID 68283765, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (3-carbamoyl-5-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (50 mg, 0.172 mmol) in DMSO (1.7 mL) was added Cs2CO3 (336 mg, 1.03 mmol). The mixture was stirred at RT for 5 min, followed by addition of methyl iodide (0.048 mL, 0.774 mmol), and stirring was continued at RT for 3 days. The reaction mixture was partitioned between water and CH2Cl2, the layers were separated and the aqueous phase was extracted twice with CH2Cl2. The combined organics were washed twice with brine, dried (phase separator) and concentrated in vacuo to afford the title compound as a yellow solid: MS (LC/MS): 305 [M+H]+, 327 [M+Na]+, 609 [2M+H]+; tR (HPLC conditions c): 4.31 min. The material thus obtained was used in the next reaction step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued at RT for 3 days
  3. customThe reaction mixture was partitioned between water and CH2Cl2
  4. customthe layers were separated
  5. extractionthe aqueous phase was extracted twice with CH2Cl2
  6. washThe combined organics were washed twice with brine
  7. customdried (phase separator)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8094053d87a48f1a8d821f16bb7fa6d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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