Trimethyl borate → HCID 89466289, compound

HRID 921053Notes

Reaction equation

HRID 921053 reaction equation
C([Li])CCC.Br[C:7]1[C:8]([CH3:33])=[C:9]([CH3:32])[CH:10]=[C:11]2[C:19]=1[N:18]=[C:17]1[N:12]2[C:13]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:14][C:15]2[N:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:21]=[CH:20][C:16]=21.B(OC)(OC)[O:35]C>C1COCC1>[OH:35][C:7]1[C:8]([CH3:33])=[C:9]([CH3:32])[CH:10]=[C:11]2[C:19]=1[N:18]=[C:17]1[N:12]2[C:13]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:14][C:15]2[N:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:21]=[CH:20][C:16]=21

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 67994867HCID 67994867, compoundHCID 178418339Butyllithium

Product 1

HCID 89466289HCID 89466289, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.2 ml (33 mmol) of n-butyllithium (2.5 M in hexane) are added dropwise with vigorous stirring to a solution, cooled to −78° C., of 13.2 g (30 mmol) of 10-bromo-3,6-di-tert-butyl-8,9-dimethyl-4,6a,11-triazabenzo[α]fluorene in 300 ml of THF, and the mixture is stirred for a further 30 min. 4.7 ml (42 mmol) of trimethyl borate are added to this solution in one portion, the mixture is stirred for a further 1 h and then allowed to warm to room temperature. The solvent is removed in vacuo, the residue is taken up in 1000 ml of ethyl acetate, the solution is cooled to 5° C., 19 ml of aqueous H2O2 solution (30% by weight) are added with vigorous stirring, and a solution of 825 mg of NaOH in 20 ml of water is then added dropwise. After stirring for 3 h, 300 ml of saturated ammonium chloride solution are added, the organic phase is separated off, washed twice with 200 ml of water each time, dried over magnesium sulfate, and the org. phase is then evaporated to a volume of about 50 ml in vacuo. 200 ml of methanol are added to the crystal slurry, the crystals are filtered off with suction and washed once with 50 ml of methanol and dried in vacuo.

Workup

  1. stirringthe mixture is stirred for a further 30 min
  2. stirringthe mixture is stirred for a further 1 h
  3. customThe solvent is removed in vacuo
  4. temperaturethe solution is cooled to 5° C.
  5. addition19 ml of aqueous H2O2 solution (30% by weight) are added with vigorous stirring
  6. additiona solution of 825 mg of NaOH in 20 ml of water is then added dropwise
  7. stirringAfter stirring for 3 h
  8. addition300 ml of saturated ammonium chloride solution are added
  9. customthe organic phase is separated off
  10. washwashed twice with 200 ml of water each time
  11. dry with materialdried over magnesium sulfate
  12. customphase is then evaporated to a volume of about 50 ml in vacuo
  13. addition200 ml of methanol are added to the crystal slurry
  14. filtrationthe crystals are filtered off with suction
  15. washwashed once with 50 ml of methanol
  16. customdried in vacuo

Sources & evidence

ORD record
ord-b93922005ebd4b2b89ba371c3ee6ec87
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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