Cesium fluoride → HCID 86761496, compound

HRID 1642417Notes

Reaction equation

HRID 1642417 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[S:26][CH:25]=[CH:24][N:19]3[C:20](=[O:23])[C:21]=2I)[CH2:3][CH2:2]1.[OH:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.[F-].[Cs+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[S:26][CH:25]=[CH:24][N:19]3[C:20](=[O:23])[C:21]=2[C:31]2[CH:32]=[CH:33][C:28]([OH:27])=[CH:29][CH:30]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 27343604-Hydroxyphenylboronic acidHCID 66753592HCID 66753592, compound

Product 1

HCID 86761496HCID 86761496, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Intermediate 2 (500 mg, 1.040 mmol), 4-hydroxyphenylboronic acid (172 mg, 1.249 mmol), Pd[(C6H5)3P]4 (120 mg, 0.104 mmol) and cesium fluoride (506 mg, 3.331 mmol) in dry THF was heated to reflux for 4.0 h. After completion of reaction, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with water, brine and dried over anhydrous Na2SO4 to afford a crude residue which was purified using 1% CH3OH in CHCl3 to afford 271 mg of the desired compound as a yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.26-0.28 (m, 2H), 0.48-0.54 (m, 2H), 1.03-1.07 (m, 1H), 3.67-3.70 (m, 2H), 3.76 (s, 3H), 6.81-6.92 (m, 3H), 6.97-7.03 (m, 3H), 7.10-7.13 (m, 2H), 7.47 (d, J=4.5 Hz, 1H), 7.95 (d, J=5.1 Hz, 1H), 8.10 (d, J=15.6 Hz, 1H), 9.57 (s, 1H); ESI-MS (m/z) 447.20 (M+H)+.

Workup

  1. temperatureto reflux for 4.0 h
  2. customAfter completion of reaction
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customto afford a crude residue which
  8. customwas purified

Sources & evidence

ORD record
ord-ab8bc2fdaf2e4610bd2619884d650e7b
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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