2-(3-(Benzo[d][1,3]dioxol-5-yl)-2-oxo-1-pentylindolin-3-yl)acetic acid → 1-pentyl-6''H-spiro[indoline-3,5''-naphtho[2,3-d][1,3]dioxole]-2,8''(7''H)-dione
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](C3(CCC(O)=O)C4C(=CC=CC=4)N(CCCCC)C3=O)=[CH:9][C:4]=2[O:3][CH2:2]1.O1C2C=C[C:37]([C:39]3(CC(O)=O)[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[N:41]([CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:40]3=[O:53])=[CH:38][C:33]=2[O:32]C1>>[CH2:48]([N:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:39]2([CH2:37][CH2:38][C:33](=[O:32])[C:8]3[C:7]2=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=3)[C:40]1=[O:53])[CH2:49][CH2:50][CH2:51][CH3:52]Participants
Procedure
Following the procedure as described in EXAMPLE 21, and making non-critical variations using 3-[3-(1,3-benzodioxol-5-yl)-2-oxo-1-pentyl-2,3-dihydro-1H-indol-3-yl]propanoic acid to replace [3-(1,3-benzodioxol-5-yl)-2-oxo-1-pentyl-2,3-dihydro-1H-indol-3-yl]acetic acid, the title compound was obtained (32%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.57 (s, 1H), 7.37-7.28 (m, 1H), 7.08-7.03 (m, 2H), 6.95 (d, 1H), 6.02 (s, 1H), 5.95-5.91 (m, 2H), 3.73 (t, 2H), 3.37-3.24 (m, 1H), 2.79-2.67(m, 1H), 2.41-2.32 (m, 2H), 1.76-1.64 (m, 2H), 1.38-1.28 (m, 4H), 0.87 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 195.4, 177.4, 152.3, 148.0, 142.7, 138.9, 133.6, 128.8, 128.4, 124.1, 122.9, 108.9, 106.9, 106.6, 101.9, 51.7, 40.2, 33.1, 32.8, 29.0, 27.1, 22.3, 14.0; MS (ES+) m/z 400.1 (M+23), 378.1 (M+1).
Sources & evidence
- ORD record
- ord-4638a346991640a7835b900be3d2f3d6
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700641B2
Reaction notes
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