6-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)one → 1'-pentyl-5-phenoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 645288Notes

Reaction equation

HRID 645288 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.Br[C:26]1[CH:31]=[CH:30][C:29]2C3(C[O:48][C:28]=2[CH:27]=1)C1C(=CC=CC=1)N(CCCCC)C3=O>>[CH2:17]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2([C:6]3[CH:7]=[C:2]([O:48][C:28]4[CH:29]=[CH:30][CH:31]=[CH:26][CH:27]=4)[CH:3]=[CH:4][C:5]=3[O:24][CH2:23]2)[C:9]1=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 592634366-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)oneHCID 592634955-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)one

Product 1

HCID 592633781'-pentyl-5-phenoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 10%

Procedure

Following the procedure as described in EXAMPLE 36, and making non-critical variations using 5-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 6-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, the title compound was obtained (10% yield) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.32-7.10 (m, 5H), 7.06-6.82 (m, 6H), 6.42 (d, 1H), 4.95 (d, 1H), 4.71 (d, 1H), 3.82-3.62 (m, 2H), 1.75-1.63 (m, 2H), 1.43-1.34 (m, 4H), 0.85 (t, 3H); MS (ES+) m/z 400.4 (M+1).

Sources & evidence

ORD record
ord-0f168e4ad891499bb582fd56996b43c5
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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