4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → HCID 68109649, compound

HRID 2179390Notes

Reaction equation

HRID 2179390 reaction equation
[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.[C:10]1([S:16]([C:19]2[CH:20]=[C:21]([CH:39]=[CH2:40])[C:22]3[O:31][C:30]4[CH2:29][CH2:28][N:27]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:26][C:25]=4[C:23]=3[CH:24]=2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl.O>[C:10]1([S:16]([C:19]2[CH:20]=[C:21]([CH2:39][CH2:40][B:4]3[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:9])([CH3:1])[O:3]3)[C:22]3[O:31][C:30]4[CH2:29][CH2:28][N:27]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:26][C:25]=4[C:23]=3[CH:24]=2)(=[O:18])=[O:17])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 68109354HCID 68109354, compound

Product 1

HCID 68109649HCID 68109649, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.05 mL, 0.33 mmol) and Rh(CO)(PPh3)2Cl (2 mg, 2.7 mmol) in dichloromethane (4 mL) at ambient temperature was added tert-butyl 8-(phenylsulfonyl)-6-vinyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (120 mg, 0.27 mmol). The reaction mixture was stirred for 4 h then diluted with water and extracted with dichloromethane. The organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate) to give tert-butyl 8-(phenylsulfonyl)-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (85 mg, 55%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.01-7.92 (m, 3H), 7.72 (br s, 1H), 7.58-7.46 (m, 3H), 4.56 (s, 2H), 3.97 (q, J=6.4 Hz, 2H), 3.83 (br s, 2H), 3.16 (t, J=6.4 Hz, 2H), 2.86 (br s, 2H), 1.51 (s, 9H), 1.39-1.19 (m, 12H).

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-c327f88367fd43469e0d2e911333278e
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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