2-Chloro-5-(chloromethyl)thiophene → HCID 59263417, compound

HRID 645241Notes

Reaction equation

HRID 645241 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[C:15]2=[CH:16][C:17]3[O:21][CH2:20][O:19][C:18]=3[CH:22]=[C:14]2[O:13][CH2:12]1.BrC1C=CC=C2C=1C1(C3=CC4OCOC=4C=C3OC1)C(=O)N2.[Cl:45][C:46]1[S:50][C:49]([CH2:51]Cl)=[CH:48][CH:47]=1.BrCC1OC(C(F)(F)F)=CC=1>>[Cl:45][C:46]1[S:50][C:49]([CH2:51][N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[C:5]3([C:15]4=[CH:16][C:17]5[O:21][CH2:20][O:19][C:18]=5[CH:22]=[C:14]4[O:13][CH2:12]3)[C:6]2=[O:11])=[CH:48][CH:47]=1

Participants

5

Reactant 4

HCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 592633724'-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1H)-oneHCID 66642701HCID 66642701, compound

Product 1

HCID 59263417HCID 59263417, compound

Procedure

Following the procedure described in EXAMPLE 10.47, and making non-critical variations using 5′-fluorospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 4′-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and 5-chloro-2-(chloromethyl)thiophene to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, the title compound was obtained (76%) as a colorless solid: mp 142-144° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.22-7.17 (m, 1H), 7.14-7.13 (m, 1H), 7.12-7.10 (m, 2H), 6.96 (d, 1H), 6.68 (s, 1H), 6.13 (s, 1H), 5.91 (d, 2H), 5.02 (ABq, 2H), 4.73 (ABq, 2H); 13C NMR (75 MHz, DMSO-d6) δ 176.9, 161.0, 157.8, 156.0, 149.0, 142.2, 138.3, 138.2 (d, 4JCF=7.0 Hz) 133.6 (d, 3JCF=33 Hz), 128.3, 127.8, 127.1, 119.5, 115.6 (d, 1JCF=93 Hz), 112.5 (d, 1JCF=100 Hz), 110.8 (d, 3JCF=32 Hz), 103.2, 102.0, 93.9, 79.8, 58.2 (d, 4JCF=7.0 Hz), 39.0; MS (ES+) m/z 430.1 (M+1).

Sources & evidence

ORD record
ord-f2d7c398e62847399024d754b77b36a5
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

Loading…