4'-bromo-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)one → 2'-Oxo-1'-pentyl-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

HRID 645292Notes

Reaction equation

HRID 645292 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:24][CH2:23][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]3=[O:22])[C:6]=2[CH:7]=1.BrC1C=CC=C2C=1C1(C3=CC4OCOC=4C=C3OC1)[C:29](=O)[N:30]2CCCCC>>[O:22]=[C:9]1[C:8]2([C:6]3[CH:7]=[C:2]([C:29]#[N:30])[CH:3]=[CH:4][C:5]=3[O:24][CH2:23]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]1[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 592633394'-bromo-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)oneHCID 592634955-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)one

Product 1

HCID 592635222'-Oxo-1'-pentyl-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

Procedure

Following the procedure as described in EXAMPLE 30, and making non-critical variations using 5-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 4′-bromo-1′-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, the title compound was obtained (78%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.51 (dt, 1H), 7.34 (dt, 1H), 7.12-6.91 (m, 5H), 5.01 (d, 1H), 4.76 (d, 1H), 3.86-3.63 (m, 2H), 1.80-1.68 (m, 2H), 1.43-1.32 (m, 4H), 0.92 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 176.2, 164.1, 142.6, 134.8, 131.4, 130.8, 129.6, 127.8, 123.9, 123.5, 118.8, 111.5, 109.1, 104.7, 80.6, 57.3, 40.6, 29.0, 27.1, 22.3, 14.0; MS (ES+) m/z 333.5 (M+1).

Sources & evidence

ORD record
ord-43c2cc87507047039bbe1145c5c2a220
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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