Water → HCID 59263468, compound

HRID 1259791Notes

Reaction equation

HRID 1259791 reaction equation
Br.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3([C:21]4=[CH:22][C:23]5[O:27][CH2:26][O:25][C:24]=5[CH:28]=[C:20]4[O:19][CH2:18]3)[C:10]2=[O:29])[CH2:4][CH2:3]1.Br[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1.C1CCN2C(=NCCC2)CC1.O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[N:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3([C:21]4=[CH:22][C:23]5[O:27][CH2:26][O:25][C:24]=5[CH:28]=[C:20]4[O:19][CH2:18]3)[C:10]2=[O:29])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66735536HCID 66735536, compound

Product 1

HCID 59263468HCID 59263468, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1′-(piperidin-4-ylmethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one hydrobromide (0.20 g, 0.44 mmol), 2-bromopyridine (0.16 mL, 0.65 mmol), tetrabutyl ammonium iodide (0.05 g) and DBU (0.16 mL, 1.09 mmol) in DMF (5.00 mL) was heated at 120° C. for 15 hrs. After cooling down to ambient temperature, water (30.0 mL) was added. The above mixture was extracted twice with ethyl acetate (50.0 mL), the combined organic phase was dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to flash chromatography eluting with 30% ethyl acetate in hexane to give a white solid (0.05 g, 27%): mp 95-97° C.; 1H NMR (300 MHz, CDCl3) δ 8.17 (d, 1H), 7.47 (td, 1H), 7.31 (t, 1H), 7.18 (d, 1H), 7.06 (t, 1H), 6.92 (d, 1H), 6.66 (d, 1H), 6.59 (dd, 1H), 6.52 (s, 1H), 6.12 (s, 1H), 5.91-5.84 (m, 2H), 4.91 (d, 1H), 4.66 (d, 1H), 4.42-4.27 (m, 2H), 3.82-3.53 (m, 2H), 2.85 (t, 2H), 2.22-2.05 (m, 1H), 1.85-1.70 (m, 2H), 1.53-1.35 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 177.9, 158.8, 156.1, 149.0, 147.4, 142.8, 142.5, 138.0, 132.4, 129.1, 124.2, 123.5, 119.5, 112.9, 108.8, 107.7, 103.1, 101.7, 93.8, 80.7, 58.3, 46.0, 45.5, 45.4, 35.2, 29.8, 29.7; MS (ES+) m/z 456 (M+1).

Workup

  1. temperatureAfter cooling down to ambient temperature
  2. extractionThe above mixture was extracted twice with ethyl acetate (50.0 mL)
  3. dry with materialthe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to dryness
  6. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5fb7f7dfe00446c0866b4e0b13b87e63
Source dataset
uspto-grants-2013_06
Patent number
US08466188B2

Reaction notes

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