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Sodium Carbonate → 4'-[6-(dimethylamino)pyridin-3-yl]-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 545871
Notes
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Reaction equation

HRID 545871 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16]1([C:32]3=[CH:33][C:34]4[O:38][CH2:37][O:36][C:35]=4[CH:39]=[C:31]3[O:30][CH2:29]1)[C:17](=[O:28])[N:18]2[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[CH:7][C:6]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16]2([C:32]4=[CH:33][C:34]5[O:38][CH2:37][O:36][C:35]=5[CH:39]=[C:31]4[O:30][CH2:29]2)[C:17](=[O:28])[N:18]3[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 592633394'-bromo-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)one

Product 1

HCID 119985854'-[6-(dimethylamino)pyridin-3-yl]-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Procedure

To an oven-dried flask was charged with [6-(dimethylamino)pyridin-3-yl]boronic acid (37.0 mg, 0.17 mmol), Pd(PPh3)4 (13.5 mg, 0.012 mmol) followed by flashing with nitrogen. To the flask was added a solution of 4′-bromo-1′-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (50.0 mg, 0.12 mmol) in anhydrous dioxane (2.00 mL) followed by the addition of 2.0 M Na2CO3 (0.24 mL). The reaction mixture was heated at reflux for 48 h. After cooling down to ambient temperature, the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate (2.00 mL), washed with saturated ammonium chloride (2.00 mL), and concentrated in vacuo to dryness. The residue was subjected to column chromatography to yield the title compounds: 1H NMR (300 MHz, CDCl3) δ 7.77 (d, 1H), 7.32 (t, 1H), 6.87 (dd, 2H), 6.71 (dd, 1H), 6.23 (d, 1H), 6.20 (s, 1H), 5.88 (d, 2H), 4.56 (ABq, 2H), 3.89-3.80 (m, 1H), 3.69-3.59 (m, 1H), 3.05 (s, 6H), 1.78-1.69 (m, 2H), 1.39-1.35 (m, 4H), 0.90 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 177.9, 158.3, 156.1, 148.8, 147.3, 142.9, 142.0, 137.8, 137.2, 129.9, 128.9, 125.6, 122.0, 121.0, 107.6, 104.3, 102.5, 101.5, 93.6, 77.8, 58.5, 40.5, 38.2, 29.1, 27.2, 22.4, 14.0; MS (ES+, m/z) 472.0 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate (2.00 mL)
  5. washwashed with saturated ammonium chloride (2.00 mL)
  6. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-7040d97b33df449181e41fded6a86c19
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935721B2

Reaction notes

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