2-(Bromomethyl)-5-(trifluoromethyl)furan → 7'-chloro-1'-((5-(trifluoromethyl)furan-2-yl)methyl)-5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-one

HRID 2385298Notes

Reaction equation

HRID 2385298 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:13][O:12][C:11]3[CH:14]=[C:15]4[C:19](=[CH:20][C:10]2=3)[CH2:18][CH2:17][O:16]4)[C:2]1=[O:21].Br[CH2:23][C:24]1[O:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=1.[Cl:33]CC1C=NC(OC)=NC=1>>[Cl:33][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[N:1]([CH2:23][C:24]1[O:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=1)[C:2](=[O:21])[C:3]12[C:10]2=[CH:20][C:19]3[CH2:18][CH2:17][O:16][C:15]=3[CH:14]=[C:11]2[O:12][CH2:13]1

Participants

4

Reactant 3

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 216981735-(Chloromethyl)-2-methoxypyrimidineHCID 592633545,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-one

Product 1

HCID 593524207'-chloro-1'-((5-(trifluoromethyl)furan-2-yl)methyl)-5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-one

Procedure

Following the procedure as described in EXAMPLE 5 and making non-critical variations using T-chloro-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-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, and 2-(bromomethyl)-5-(trifluoromethyl)furan to replace 5-(chloromethyl)-2-methoxypyrimidine, 7′-chloro-1′-((5-(trifluoromethyl)furan-2-yl)methyl)-5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3′-indolin]-2′-one was obtained (30%) as a colorless solid: mp 210-211° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ7.34-7.31 (m, 1H), 7.21-7.16 (m, 2H), 7.10-7.05 (m, 1H), 6.67-6.65 (m, 1H), 6.49 (s, 1H), 6.43 (s, 1H), 5.34 (s, 2H), 4.85 (d, J=9.6 Hz, 1H), 4.74 (d, J=9.6 Hz, 1H), 4.57-4.48 (m, 2H), 2.94 (t, J=3.0 Hz, 2H); 13C NMR (75 MHz, DMSO-d6) δ177.4, 161.2, 160.4, 154.1, 139.4, 138.9, 137.2, 135.4, 130.5, 124.6, 122.8, 120.6, 120.1, 119.9, 118.7, 117.1, 114.3, 114.2, 108.7, 92.4, 79.8, 72.0, 56.6, 28.1.

Sources & evidence

ORD record
ord-bcd6aabd2655400fb9df2afd7b4dd5a6
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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