Hexane → HCID 67147593, compound

HRID 490498Notes

Reaction equation

HRID 490498 reaction equation
C([Li])[CH2:2][CH2:3][CH3:4].I[C:7]1[C:15]2[C:10](=[C:11]([O:18][CH3:19])[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]([C:20]([OH:22])=[O:21])[CH:8]=1.[B:23](OCCCC)([O:29]CCCC)[O:24]CCCC.[CH3:39]CCCCC>O1CCCC1>[C:3]([O:22][C:20]([N:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:7]([B:23]([OH:29])[OH:24])=[CH:8]1)=[O:21])([CH3:2])([CH3:4])[CH3:39]

Participants

6

Reactant 4

HCID 8058HexaneHCID 12712Tributyl borateHCID 67147753HCID 67147753, compoundHCID 178418339Butyllithium

Product 1

HCID 67147593HCID 67147593, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

9.82 ml of a 2.5N solution of n-butyllithium in hexane are added, dropwise, while maintaining the temperature at around −100° C., to a solution of 2.2 g of tert-butyl ester of 3-iodo-5,7-dimethoxyindole-1-carboxylic acid and 1.8 ml of tributyl borate in 33 ml of tetrahydrofuran cooled to −100° C. The cooling bath is removed and, when the temperature of the reaction medium reaches approximately −5° C., 2 g of ice are added. After agitation for one hour at a temperature in the region of 20° C., the mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is extracted with 200 ml of ethyl acetate, and washed with 100 ml of a saturated aqueous sodium chloride solution The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). 2.34 g of 1-tert-butyloxycarbonyl-5,7-dimethoxy-1H-indole-3-boronic acid are thus obtained in the form of a solid, which is used as it is for the following step.

Workup

  1. customThe cooling bath is removed
  2. custommedium reaches approximately −5° C.
  3. addition2 g of ice are added
  4. concentrationthe mixture is concentrated to dryness under reduced pressure (13 kPa)
  5. extractionThe residue is extracted with 200 ml of ethyl acetate
  6. washwashed with 100 ml of a saturated aqueous sodium chloride solution The organic phase
  7. dry with materialis dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-d785a4e2b43d4a13bf06696cf0dd0451
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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