Triisopropyl borate → 1-cyclopentyl-5-fluoro-3-(methoxycarbonyl)-6-methyl-1H-indol-2-ylboronic acid

HRID 1028021Notes

Reaction equation

HRID 1028021 reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][C:11]([F:16])=[C:12]([CH3:15])[CH:13]=3)[C:8]([C:17]([O:19][CH3:20])=[O:18])=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:24][B:25](OC(C)C)[O:26]C(C)C)(C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][C:11]([F:16])=[C:12]([CH3:15])[CH:13]=3)[C:8]([C:17]([O:19][CH3:20])=[O:18])=[C:7]2[B:25]([OH:26])[OH:24])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 66730594methyl 1-cyclopentyl-5-fluoro-6-methyl-1H-indole-3-carboxylate

Product 1

HCID 667309151-cyclopentyl-5-fluoro-3-(methoxycarbonyl)-6-methyl-1H-indol-2-ylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of methyl 1-cyclopentyl-5-fluoro-6-methyl-1H-indole-3-carboxylate (2.64 g, 9.6 mmol) and triisopropylborate (4.0 mL, 17.28 mmol) in THF (40 mL) at −78° C. was added LDA (1.5 M, 8.3 mL, 12.48 mmol) dropwise. The mixture was stirred for 45 min, and then treated with ice water and extracted with dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 1-cyclopentyl-5-fluoro-3-(methoxycarbonyl)-6-methyl-1H-indol-2-ylboronic acid as a semi-solid (3.1 g, ˜50% pure), which was used in next step without further purification.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-1a285fa56851494c99890dcea37afbda
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

Loading…