Water → HCID 20827141, compound

HRID 1454317Notes

Reaction equation

HRID 1454317 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH:10]=[C:11](B3CC(C)(C)C(C)(C)O3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.O.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH:33]=[C:32](OS(C(F)(F)F)(=O)=O)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].[Li+].[Cl-]>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([O:26][C:27]([N:29]1[CH2:30][CH:31]=[C:32]([C:11]2[C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[O:9][CH:10]=2)[CH2:33][CH2:34]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 433294Lithium ChlorideHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 22326941HCID 22326941, compound

Product 1

HCID 20827141HCID 20827141, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-(7-methoxybenzo[b]furan-3-yl)-4,4,5,5-tetramethyl-[1,2]oxaborolane (1.10 g, 4.0 mmol) in dimethoxyethane (1 mL) was added CsCO3 (0.650 g, 2.0 mmol), H2O (1 mL), 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.480 g, 1.45 mmol), LiCl (0.10 g, 2.4 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.06 g, 0.05 mmol). The reaction was heated in the microwave for 5 min at 150° C. The solvent was removed in vacuum, the residue taken up in 300 mL of methylene chloride, washed with 200 mL portions of saturated aqueous sodium carbonate and 1 N NH4OH (aq), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was filtered through 150 mL of silica gel with 15% ethyl acetate/hexane as eluant to give 0.50 g of the title compound. 1 H NMR (300 MHz, CDCl3); δ 1.5 (s, 9H), 2.51 (t, 2H), 3.66 (t, 2H), 4.04 (s, 3H), 4.12 (dd,2H), 6.24 (brs, 1H), 6.91 (d, 1H), 7.17 (t, 1H), 7.39 (d, 1H), 7.59 (s, 1H), MS (ES) m/z (relative intensity): 330 (M+H,100).

Workup

  1. customThe solvent was removed in vacuum
  2. washwashed with 200 mL portions of saturated aqueous sodium carbonate and 1 N NH4OH (aq)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. filtrationThe residue was filtered through 150 mL of silica gel with 15% ethyl acetate/hexane as eluant

Sources & evidence

ORD record
ord-c0a5a88b653a4cf484c5a0468d20b305
Source dataset
uspto-grants-2009_01
Patent number
US07479500B2

Reaction notes

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