(1-(tert-Butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid → (4-fluoro-1H-indol-2-yl)boronic acid

HRID 595542Notes

Reaction equation

HRID 595542 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[B:18]([OH:20])[OH:19])=O)(C)(C)C>C(O)(C(F)(F)F)=O>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[C:9]([B:18]([OH:20])[OH:19])[NH:8]2

Participants

3

Reactant 1

HCID 44118245(1-(tert-Butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid

Product 1

HCID 90333436(4-fluoro-1H-indol-2-yl)boronic acidYield 94%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

TFA (60 mL) was added 1-(tert-butoxycarbonyl)-4-fluoro-1H-indol-2-ylboronic acid (10 g, 35.83 mmol) in portions at 0° C. and then the mixture was stirred at room temperature for 3 hours. The mixture was poured into ice water, stirred for 10 minutes and filtered through a pad to give the crude 4-fluoro-1H-indol-2-ylboronic acid (6.0 g, yield: 94%) without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 11.09 (s, 1H), 8.35 (br s, 2H), 7.22 (d, J=8.00 Hz, 1H), 7.02˜7.07 (m, 2H), 6.68˜6.72 (m, 1H). MS (M+H)+: 180.

Workup

  1. stirringstirred for 10 minutes
  2. filtrationfiltered through a pad

Sources & evidence

ORD record
ord-0b5b8cd03a0144b6bc752126ed490466
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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