2-(Bromomethyl)pyridine hydrobromide → 6-Methoxy-2'-oxo-1'-(pyridin-2-ylmethyl)-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile
Reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.BrCC1OC(C(F)(F)F)=CC=1.[CH3:21][O:22][C:23]1[C:28]([C:29]#[N:30])=[CH:27][C:26]2[C:31]3([CH2:41][O:42][C:25]=2[CH:24]=1)[C:39]1[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=1)[NH:33][C:32]3=[O:40].CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1>>[CH3:21][O:22][C:23]1[C:28]([C:29]#[N:30])=[CH:27][C:26]2[C:31]3([CH2:41][O:42][C:25]=2[CH:24]=1)[C:39]1[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=1)[N:33]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[C:32]3=[O:40]Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 9 and making non-critical variations using 2-(bromomethyl)pyridine hydrobromide to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, and 6-methoxy-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, 6-methoxy-2′-oxo-1′-(pyridin-2-ylmethyl)-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (80%): mp 187-189° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.57-8.55 (m, 1H), 7.70-7.64 (m, 1H), 7.27-7.20 (m, 3H), 7.12-7.00 (m, 3H), 6.91-6.89 (m, 1H), 6.55 (s, 1H), 4.97 (ABq, 2H), 3.90 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 176.7, 165.8, 164.1, 154.9, 149.6, 142.3, 137.1, 131.2, 129.4, 128.8, 123.7, 123.6, 122.9, 122.0, 121.7, 116.7, 109.8, 94.6, 81.2, 56.9, 56.3, 45.9; MS (ES+) m/z 383.8 (M+1).
Sources & evidence
- ORD record
- ord-b1ac0a34e73c415ba6c5c994df62a424
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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