6-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)one → HCID 59263501, compound

HRID 645293Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:30][CH2:29][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[F:27])=[O:19])[C:9]3=[O:28])[C:6]=2[CH:7]=1.BrC1C=CC2C3(COC=2C=1)C1C(=CC=CC=1)[N:40]([CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])C3=O>>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:20][C:18](=[O:19])[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]([C:50]4[CH:51]=[N:40][CH:47]=[CH:48][CH:49]=4)[CH:3]=[CH:4][C:5]=3[O:30][CH2:29]2)[C:9]1=[O:28]

Participants

Reactant 2

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

HCID 59263486HCID 59263486, compound

Product 1

HCID 59263501HCID 59263501, compoundYield 55%

Procedure

Following the procedure as described in EXAMPLE 37, and making non-critical variations using 2-(5-bromo-2′-oxospiro[1-benzofuran-3,3′-indol]-1′(2′H)-yl)-N-(2-fluorophenyl)acetamide to replace 6-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, the title compound was obtained (55% yield) was obtained as a white solid: mp 98-100° C.; 1H NMR (300 MHz, CDCl3) δ 8.60-8.53 (m, 2H), 8.14 (dd, 1H), 7.65 (dd, 1H), 7.41 (dd, 1H), 7.32-6.90 (m, 11H), 5.02 (d, 1H), 4.76 (d, 1H), 4.72 (d, 1H), 4.56 (d, 1H); 13C NMR (75 MHz, CDCl3) δ 177.9, 164.8, 160.9, 154.2, 151.0, 147.1, 141.7, 134.2, 131.7, 131.5, 129.9, 129.4, 129.1, 125.1, 124.6, 124.5, 124.2, 124.0, 122.5, 122.2, 115.1, 114.8, 111.0, 109.1, 80.0, 58.1, 44.6; MS (ES+) m/z 466.4 (M+1).

Sources & evidence

ORD record: ord-b65ddc26f5b24846a6e7331e5e304fbe
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700641B2

Reaction notes

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