Tetrahydrofuran → N-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-amine

HRID 928632Notes

Reaction equation

HRID 928632 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][CH2:7]2.C1COCC1.[Li]CCCC.[Li]C(C)(C)C.C(O[B:37]1[O:41][C:40]([CH3:43])([CH3:42])[C:39]([CH3:45])([CH3:44])[O:38]1)(C)C>CCCCC>[C:12]1([NH:11][CH:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[B:37]3[O:41][C:40]([CH3:43])([CH3:42])[C:39]([CH3:45])([CH3:44])[O:38]3)[CH2:7][CH2:8]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1180726057-Bromo-2,3-dihydro-N-phenyl-1h-inden-1-amineHCID 178418306HCID 178418306, compoundHCID 178418339Butyllithium

Product 1

HCID 123849583N-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-amine

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a solution of 2.50 g (8.70 mmol) of 7-bromo-N-phenyl-2,3-dihydro-1H-inden-1-amine in 50 ml THF 3.50 ml (8.70 mmol) of 2.5M nBuLi in hexanes was added at −80° C. in argon atmosphere. The reaction mixture was then stirred for 1 h at this temperature. Further on, 11.1 ml (17.8 mmol) of 1.7M tBuLi in pentane was added, and the reaction mixture was stirred for 1 h. Then, 3.23 g (17.4 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added. After that the cooling bath was removed, and the resulting mixture was stirred for 1 h at room temperature. To the formed mixture 10 ml of water was added, and the resulting mixture was evaporated to dryness. The residue was diluted with 200 ml of water, and the title product was extracted with 3×50 ml of ethyl acetate. The combined organic extract was dried over Na2SO4 and evaporated to dryness. Yield 2.80 g (96%) of a light yellow oil. Anal. calc. For C21H26BNO2: C, 75.24; H, 7.82; N, 4.18. Found: C, 75.40; H, 8.09; N, 4.02. 1H NMR (CDCl3): δ 7.63 (m, 1H, 6-H in indane); 7.37-7.38 (m, 1H, 4-H in indane); 7.27-7.30 (m, 1H, 5-H in indane); 7.18 (m, 2H, 3,5-H in phenyl); 6.65-6.74 (m, 3H, 2,4,6-H in phenyl); 5.20-5.21 (m, 1H, 1-H in indane); 3.09-3.17 (m, 1H, 3- or 3′-H in indane); 2.85-2.92 (m, 1H, 3′- or 3-H in indane); 2.28-2.37 (m, 1H, 2- or 2′-H in indane); 2.13-2.19 (m, 1H, 2′- or 2-H in indane); 1.20 (s, 6-H, 4,5-Me in BPin); 1.12 (s, 6H, 4′,5′-Me in BPin).

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. customAfter that the cooling bath was removed
  3. stirringthe resulting mixture was stirred for 1 h at room temperature
  4. additionTo the formed mixture 10 ml of water was added
  5. customthe resulting mixture was evaporated to dryness
  6. additionThe residue was diluted with 200 ml of water
  7. extractionthe title product was extracted with 3×50 ml of ethyl acetate
  8. extractionThe combined organic extract
  9. dry with materialwas dried over Na2SO4
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-2193562dfb10435fb760a7f55ebf79db
Source dataset
uspto-grants-2016_03
Patent number
US09290519B2

Reaction notes

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