Sodium Carbonate → HCID 178451606, compound

HRID 1807616Notes

Reaction equation

HRID 1807616 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[CH:6]2)#[N:2].Cl.[NH2:20][OH:21].C([O-])([O-])=O.[Na+].[Na+]>CCO>[OH:21][NH:20][C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[CH:6]2)=[NH:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 72133321-Boc-5-cyanoindole

Product 1

HCID 178451606HCID 178451606, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Prepared using General Procedure 1. To a flask containing tert-butyl 5-cyano-1H-indole-1-carboxylate INT-65 (200 mg, 0.73 mmol) was added EtOH (6 mL), hydroxylamine hydrochloride (177 mg, 2.54 mmol) and Na2CO3 (154 mg, 1.45 mmol). The mixture was stirred at 75° C. overnight then concentrated, re-dissolved in DCM and washed with NaHCO3. The combined organic layers were dried over Na2SO4 and concentrated to provide 222 mg of crude tert-butyl 5-(N-hydroxycarbamimidoyl)-1H-indole-1-carboxylate INT-66 as a white solid which was used directly in the next experiment. LCMS-ESI (m/z) calculated for C14H17N3O3: 275.3; found 276.1 [M+H]+, tR=2.25 min.

Workup

  1. customPrepared
  2. concentrationthen concentrated
  3. dissolutionre-dissolved in DCM
  4. washwashed with NaHCO3
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-86269bdf6d744588992b429c84f916ac
Source dataset
uspto-grants-2013_01
Patent number
US08357706B2

Reaction notes

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