2-(Bromomethyl)tetrahydro-2H-pyran → 1'-[(5-chloro-2-thienyl)methyl]-7'-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 2385253Notes

Reaction equation

HRID 2385253 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7]Cl)=[CH:5][CH:6]=1.BrCC1CCCCO1.[F:17][C:18]([F:41])([F:40])[C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[NH:26][C:25](=[O:28])[C:24]12[C:32]2=[CH:33][C:34]3[O:38][CH2:37][O:36][C:35]=3[CH:39]=[C:31]2[O:30][CH2:29]1>>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:26]2[C:27]3[C:23](=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]([F:40])([F:17])[F:41])[C:24]3([C:32]4=[CH:33][C:34]5[O:38][CH2:37][O:36][C:35]=5[CH:39]=[C:31]4[O:30][CH2:29]3)[C:25]2=[O:28])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 685972007'-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 593521971'-[(5-chloro-2-thienyl)methyl]-7'-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

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 7′-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-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′-[(5-chloro-2-thienyl)methyl]-7′-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one was obtained (95%) as a colorless solid: mp 165-166° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.66 (d, J=8.0 Hz, 1H), 7.49 (d, J=7.2 Hz, 1H), 7.24 (dd, J=7.8, 7.8 Hz, 1H), 6.93 (d, J=3.8 Hz, 1H), 6.80 (d, J=3.8 Hz, 1H), 6.70 (s, 1H), 6.22 (s, 1H), 5.91 (d, J=4.4 Hz, 2H), 5.09 (ABq, 2H), 4.78 (ABq, 2H); 13C NMR (75 MHz, DMSO-d6) δ178.9, 156.2, 149.2, 142.4, 139.9 (2C), 138.7, 135.4, 129.1, 127.4, 127.2, 126.9, 125.9, 123.9, 119.4, 111.5, 103.5, 102.0, 93.9, 80.7, 56.5, 42.3; MS (ES+) m/z 481.2 (M+1), 479.9 (M+1).

Sources & evidence

ORD record
ord-2e19900945d54cc3ac06e74b253446a8
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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