5-(Bromomethyl)-2,1,3-benzoxadiazole → 1'-(2,1,3-benzoxadiazol-5-ylmethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 545907Notes

Reaction equation

HRID 545907 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:13]3=[CH:14][C:15]4[O:19][CH2:18][O:17][C:16]=4[CH:20]=[C:12]3[O:11][CH2:10]2)[C:2]1=[O:21].CC1(C)COC2=CC3OCC4(C=3C=C12)C1C(=CC=CC=1)NC4=O.Br[CH2:46][C:47]1[CH:55]=[CH:54][C:50]2=[N:51][O:52][N:53]=[C:49]2[CH:48]=1.BrCC1OC(C(F)(F)F)=CC=1>>[N:51]1[O:52][N:53]=[C:49]2[CH:48]=[C:47]([CH2:46][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]4([C:13]5=[CH:14][C:15]6[O:19][CH2:18][O:17][C:16]=6[CH:20]=[C:12]5[O:11][CH2:10]4)[C:2]3=[O:21])[CH:55]=[CH:54][C:50]=12

Participants

5

Reactant 4

HCID 27355875-(Bromomethyl)-2,1,3-benzoxadiazoleHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 592634705,5-dimethyl-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1H)-one

Product 1

HCID 592634451'-(2,1,3-benzoxadiazol-5-ylmethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Procedure

Following the procedure described in EXAMPLE 10.21, and making non-critical variations using spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 5,5-dimethyl-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, and 5-(bromomethyl)benzo[c][1,2,5]oxadiazole to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, the title compound was obtained (17%) as a white solid: mp 163-165° C.; MS (ES+) m/z 414.4 (M+1).

Sources & evidence

ORD record
ord-fa19f9c2109d405e89441f7f34e009be
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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