Hydrochloric Acid → HCID 59800131, compound

HRID 1037582Notes

Reaction equation

HRID 1037582 reaction equation
C([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)(OC(C)(C)C)=O.[B:22](OC(C)C)([O:27]C(C)C)[O:23]C(C)C.[Li+].CC([N-]C(C)C)C.Cl>C1(C)C=CC=CC=1.C1COCC1.O>[B:22]([C:9]1[NH:8][C:16]2[C:11]([CH:10]=1)=[CH:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=2)([OH:27])[OH:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 11818572HCID 11818572, compound

Product 1

HCID 59800131HCID 59800131, compoundYield 65.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

150 g (519 mmol) of N-Boc-5-ethoxycarbonylindole and 192 ml (833 mmol) of triisopropyl borate in 350 ml of toluene were admixed at from 5° C. to 10° C. with 350 ml of a 1.8 molar solution of LDA in THF. The mixture was stirred for a further 5 min and the reaction mixture was added to a solution of 278 g of 30% hydrochloric acid and 940 ml of water. Subsequently, the mixture was stirred at from 5° C. to 10° C. for 30 min. Thereafter, the mixture was filtered and the filtercake was suspended in 530 ml of ethanol. This suspension was added at 40° C. to a solution of 500 ml of 30% hydrochloric acid and 224 ml of ethanol. Subsequently, the mixture was stirred at from 40° C. to 45° C. for 2.5 h and admixed at 30° C. with 380 ml of water. The mixture was then cooled to from 10° C. to 15° C., stirred at this temperature for 30 min and filtered. Drying under reduced pressure afforded 79.5 g (61% of theory) of 2-borono-5-ethoxycarbonylindole (HPLC: 92.7 area %).

Workup

  1. stirringSubsequently, the mixture was stirred at from 5° C. to 10° C. for 30 min
  2. filtrationThereafter, the mixture was filtered
  3. additionThis suspension was added at 40° C. to a solution of 500 ml of 30% hydrochloric acid and 224 ml of ethanol
  4. stirringSubsequently, the mixture was stirred at from 40° C. to 45° C. for 2.5 h
  5. customadmixed at 30° C. with 380 ml of water
  6. temperatureThe mixture was then cooled to from 10° C. to 15° C.
  7. stirringstirred at this temperature for 30 min
  8. filtrationfiltered
  9. customDrying under reduced pressure

Sources & evidence

ORD record
ord-5edf48c70608486a8b9bcf7b9bf67581
Source dataset
uspto-grants-2013_10
Patent number
US08546567B2

Reaction notes

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