Trifluoroacetic acid → HCID 67357639, compound

HRID 1407518Notes

Reaction equation

HRID 1407518 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:6](=[O:18])[C:5]2(O)[C:19]1[C:28]([OH:29])=[CH:27][C:22]2[O:23][CH2:24][CH2:25][O:26][C:21]=2[CH:20]=1.FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:6](=[O:18])[CH:5]2[C:19]1[C:28]([OH:29])=[CH:27][C:22]2[O:23][CH2:24][CH2:25][O:26][C:21]=2[CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68599379HCID 68599379, compound

Product 1

HCID 67357639HCID 67357639, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Procedure

To a suspension of 5-bromo-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-(pyridin-2-ylmethyl)-1,3-dihydro-2H-indol-2-one (3.60 g, 8.10 mmol) in triethylsilane (10 mL) at 0° C. was added trifluoroacetic acid (40 mL). The solution was allowed to warm to ambient temperature over 2 h and was stirred for a further 4 h. The reaction mixture was concentrated in vacuo and saturated aqueous sodium bicarbonate and ethyl acetate were added to the residue, causing a precipitate to be deposited. The solid was collected by filtration and washed sequentially with diethyl ether and hexanes to afford 5-bromo-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-(pyridin-2-ylmethyl)-1,3-dihydro-2H-indol-2-one (4.03 g, 100%) as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 8.59-8.55 (m, 1H), 7.90-7.80 (m, 1H), 7.44-7.37 (m, 1H), 7.34-7.27 (m, 1H), 7.07 (s, 1H), 6.82-6.68 (m, 2H), 6.27 (s, 1H), 5.17-4.93 (m, 2H), 4.84 (s, 1H), 4.23-4.06 (m, 4H). MS (ES+) m/z 452.9 (M+1), 454.9 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and saturated aqueous sodium bicarbonate and ethyl acetate
  2. additionwere added to the residue
  3. filtrationThe solid was collected by filtration
  4. washwashed sequentially with diethyl ether and hexanes

Sources & evidence

ORD record
ord-f5add4de62c64e89b43c08e9f4e81729
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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