2-(Bromomethyl)tetrahydro-2H-pyran → HCID 59352287, compound

HRID 1965567Notes

Reaction equation

HRID 1965567 reaction equation
Br.Br[CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.BrCC1CCCCO1.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([C:37]3[C:33]4=[N:34][O:35][N:36]=[C:32]4[CH:31]=[CH:30][C:29]=3[O:28][CH2:27]2)[C:19]1=[O:38]>>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3([C:37]4[C:33]5=[N:34][O:35][N:36]=[C:32]5[CH:31]=[CH:30][C:29]=4[O:28][CH2:27]3)[C:19]2=[O:38])[CH:5]=1

Participants

4

Reactant 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 593526377H-spiro[benzofuro[4,5-c][1,2,5]oxadiazole-8,3'-indolin]-2'-one

Product 1

HCID 59352287HCID 59352287, compound

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using 3-(bromomethyl)pyridine hydrobromide to replace 2-(bromomethyl)tetrahydro-2H-pyran, and spiro[furo[3,2-e][2,1,3]benzoxadiazole-8,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 1′-(pyridin-3-ylmethyl)spiro[furo[3,2-e][2,1,3]benzoxadiazole-8,3′-indol]-2′(1′H)-one was obtained (47%) as a colorless solid: mp 230-232° C.; 1H NMR (300 MHz, CDCl3) δ 8.74 (s, 1H), 8.59 (d, J=2.7 Hz, 1H), 7.88-7.82 (m, 2H), 7.39-7.16 (m, 4H), 7.04 (dd, J=7.5, 7.5 Hz, 1H), 6.80 (d, J=7.8 Hz, 1H), 5.35-5.24 (m, 2H), 4.99 (d, J=9.3 Hz, 1H), 4.84 (d, J=15.9 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ176.1, 162.9, 149.4, 148.8, 148.3, 144.8, 141.7, 135.1, 130.8, 129.8, 129.7, 123.9, 121.8, 119.4, 109.6, 106.9, 81.9, 57.2, 42.0; MS (ES+) m/z 371.1 (M+1).

Sources & evidence

ORD record
ord-0802f9dba50746419c60e5cae41e8df6
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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