tert-Butanol → HCID 22612547, compound

HRID 844433Notes

Reaction equation

HRID 844433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.C(N1C=CN=C1)(N1C=CN=C1)=O.C1CCN2C(=NCCC2)CC1.[C:37](O)([CH3:40])([CH3:39])[CH3:38]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:12])=[CH:5]2

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 826935-Chloro-1H-indole-2-carboxylic acid

Product 1

HCID 22612547HCID 22612547, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

5.52 g of 5-chloro-2-indolecarboxylic acid are dissolved in 40 ml of DMF, 4.57 g of carbonyldiimidazole are added at RT, under nitrogen, the mixture is then heated to 40° C and 4.3 g of DBU and 4.17 g of tertbutanol are added. Heating is continued at 40° C. for 3 hours, the precipitate formed is then filtered off and the filtrate is concentrated under vacuum. The residue is taken up in EtOAc, washed with 10% Na2CO3 solution, with saturated aqueous NaCl, with sulphate buffer and then dried over Na2SO4 and concentrated. The residue is chromatographed on silica, eluting with DCM, to give 0.45 g of the expected compound: m.p.=140-142° C.

Workup

  1. temperatureHeating
  2. customthe precipitate formed
  3. filtrationis then filtered off
  4. concentrationthe filtrate is concentrated under vacuum
  5. washwashed with 10% Na2CO3 solution, with saturated aqueous NaCl, with sulphate buffer
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica
  9. washeluting with DCM

Sources & evidence

ORD record
ord-41c3147bbdfa43ec9dd93596d8f154ae
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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