Sodium Carbonate → HCID 86604970, compound

HRID 1714056Notes

Reaction equation

HRID 1714056 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH:21]3[O:25][CH2:24][CH2:23][O:22]3)[C:8]=2[C:26]2[CH:31]=[CH:30][C:29](OC)=[CH:28][C:27]=2[CH:34]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:43][OH:44]>CCO>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH:21]3[O:22][CH2:23][CH2:24][O:25]3)[C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH:34]=[N:43][OH:44])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86604962methyl 3-cyclohexyl-1-(1,3-dioxolan-2-ylmethyl)-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxylate

Product 1

HCID 86604970HCID 86604970, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of methyl methyl 3-cyclohexyl-1-(1,3-dioxolan-2-ylmethyl)-2-(2-formylphenyl)-1H-indole-6-carboxylate (prepared in analogous fashion to Example 4, Step 2, using 2-formylphenylboronic acid) in EtOH (0.05 M), were added aqueous solutions of sodium carbonate (2M; 1.3 eq) followed by hydroxylamine hydrochloride (2M; 1.3 eq). The reaction was stirred at RT for 2 h, before the EtOH was reduced in vacuo and the residue partitioned between EtOAc and water. The aqueous fraction was extracted a second time with EtOAc and the combined organics washed with water and then brine before being dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (95%); MS (ES+) m/z 463 (M+H)+.

Workup

  1. customthe residue partitioned between EtOAc and water
  2. extractionThe aqueous fraction was extracted a second time with EtOAc
  3. washthe combined organics washed with water
  4. dry with materialbrine before being dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4462fcbf7d934250acc96298d8bf916f
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

Loading…