4-Fluorobenzene-1,2-diamine → HCID 178517568, compound

HRID 425736Notes

Reaction equation

HRID 425736 reaction equation
[O:1]=[C:2]1[C:10]2([C:14]3=[CH:15][C:16]4[O:20][CH2:19][O:18][C:17]=4[CH:21]=[C:13]3[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][C:23](O)=O.[F:26][C:27]1[CH:28]=[C:29]([NH2:34])[C:30]([NH2:33])=[CH:31][CH:32]=1>C1(C)C=CC=CC=1.O>[F:26][C:27]1[CH:32]=[CH:31][C:30]2[NH:33][C:23]([CH2:22][N:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:10]4([C:14]5=[CH:15][C:16]6[O:20][CH2:19][O:18][C:17]=6[CH:21]=[C:13]5[O:12][CH2:11]4)[C:2]3=[O:1])=[N:34][C:29]=2[CH:28]=1

Participants

5

Reactant 2

HCID 1645844-Fluorobenzene-1,2-diamineHCID 59263364(2'-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-1'(2'H)-yl)acetic acid

Product 1

HCID 178517568HCID 178517568, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of (2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)acetic acid (0.50 g, 1.47 mmol) and 4-fluorobenzene-1,2-diamine (0.15 g, 1.18 mmol) in anhydrous toluene (20.0 mL) was refluxed overnight under N2. The reaction mixture was diluted with water (250 mL) and extracted with ethyl acetate (2×200 mL). The combined organic extracts was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (ethyl acetate/hexane, 2/1) to give the title compound (0.13 g, 22%): mp 138-142° C.; 1H NMR (300 MHz, CDCl3) δ 7.47-7.39 (m, 1H), 7.32-7.22 (m, 2H), 7.16-6.93 (m, 3H), 6.18 (s, 1H), 6.07 (s, 1H), 5.84-5.78 (m, 2H), 5.20-5.14 (m, 2H), 4.98 (d, 1H), 4.60 (d, 1H); 13C NMR (75 MHz, CDCl3) δ 179.2, 161.3, 158.1, 156.2, 149.2, 149.1, 142.5, 141.2, 131.5, 129.5, 124.4, 124.0, 118.0, 111.6, 111.2, 109.9, 103.1, 101.7, 93.5, 80.5, 58.5, 38.9; MS (ES+) m/z 430.2 (M+1).

Workup

  1. temperaturewas refluxed overnight under N2
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. dry with materialThe combined organic extracts was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-927ea44f7eff4f86823ce06243dcb620
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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