Borate → HCID 71089571, compound

HRID 710082Notes

Reaction equation

HRID 710082 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[C:12]([F:19])[CH:11]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Li]CCCC.[B:25]([O-])([O-:27])[O-:26]>C1COCC1>[C:14]([C:13]1[CH:17]=[CH:18][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][C:2]([B:25]([OH:27])[OH:26])=[CH:3][C:4]=3[CH:9]=2)=[CH:11][C:12]=1[F:19])(=[O:15])[NH2:16]

Participants

5

Reactant 3

HCID 26574BorateHCID 71089573HCID 71089573, compoundHCID 178418339Butyllithium

Product 1

HCID 71089571HCID 71089571, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Intermediate 20 (100 mg 0.4 mmol) was dissolved in THF (10 ml) and this mixture was cooled to −78° C. under N2 atmosphere. n-BuLi (0.5 ml, 1.3 mmol) was added to the above mixture and stirred at same temperature for 20 mins Reaction mixture warmed to 0° C. and stirred for 2 hrs. After that trisopropyl borate (88 mg, 0.47 mmol) was added and stirred the reaction for 16 h at rt. Reaction mass quenched with 2N HCl worked it up (EtOAC/H2O) to afford the titled compound (110 mg) as a crude. It was used in the next step without further purification.

Workup

  1. customReaction mixture
  2. temperaturewarmed to 0° C.
  3. stirringstirred for 2 hrs
  4. stirringstirred
  5. customthe reaction for 16 h at rt
  6. customReaction mass
  7. customquenched with 2N HCl

Sources & evidence

ORD record
ord-cb1c02d5ca5741a2a92b8919da7bfc48
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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