2-(Bromomethyl)tetrahydro-2H-pyran → 1'-[(5-Chloro-2-thienyl)methyl]-2'-oxo-1',2'-dihydrospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indole]-7'-carbonitrile

HRID 1965533Notes

Reaction equation

HRID 1965533 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7]Cl)=[CH:5][CH:6]=1.BrCC1CCCCO1.[O:17]=[C:18]1[C:26]2([C:30]3=[CH:31][C:32]4[O:36][CH2:35][O:34][C:33]=4[CH:37]=[C:29]3[O:28][CH2:27]2)[C:25]2[C:20](=[C:21]([C:38]#[N:39])[CH:22]=[CH:23][CH:24]=2)[NH:19]1>>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][C:21]=3[C:38]#[N:39])[C:26]3([C:30]4=[CH:31][C:32]5[O:36][CH2:35][O:34][C:33]=5[CH:37]=[C:29]4[O:28][CH2:27]3)[C:18]2=[O:17])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 593522642'-Oxo-1',2'-dihydrospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indole]-7'-carbonitrile

Product 1

HCID 593521571'-[(5-Chloro-2-thienyl)methyl]-2'-oxo-1',2'-dihydrospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indole]-7'-carbonitrile

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using 2-chloro-5-(chloromethyl)thiophene to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 2′-oxo-1′,2′-dihydrospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indole]-7′-carbonitrile to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 1′-[(5-chloro-2-thienyl)methyl]-2′-oxo-1′,2′-dihydrospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indole]-7′-carbonitrile was obtained (78%) as a colorless solid: mp 192-193° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 7.72 (dd, J=8.0, 1.1 Hz, 1H), 7.54 (dd, J=7.4, 1.1 Hz, 1H), 7.21 (dd, J=7.7, 7.7 Hz, 1H), 7.03 (s, 2H), 6.73 (s, 1H), 6.35 (s, 1H), 5.95 (dd, J=4.0, 0.7 Hz, 2H), 5.29 (d, J=1.5 Hz, 2H), 4.78 (dd, J=20.4, 9.6 Hz, 2H); 13C NMR (75 MHz, DMSO-d6) δ 177.0, 155.5, 148.7, 143.2, 141.8, 137.6, 133.6, 133.2, 128.8, 127.9, 126.6, 126.5, 123.7, 118.5, 116.9, 103.0, 101.5, 93.4, 92.6, 79.5, 56.4, 40.0; MS (ES+) m/z 437.3 (M+1), 439.3 (M+1).

Sources & evidence

ORD record
ord-23ba86f30a654ab189985f653e94cdc9
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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