2-(Bromomethyl)-5-(trifluoromethyl)furan → HCID 59352582, compound

HRID 1965627Notes

Reaction equation

HRID 1965627 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].CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1.Br[CH2:45][C:46]1[O:47][C:48]2[C:54]([F:55])=[CH:53][CH:52]=[CH:51][C:49]=2[CH:50]=1.BrCC1OC(C(F)(F)F)=CC=1>>[F:55][C:54]1[C:48]2[O:47][C:46]([CH2:45][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]4([CH2:13][O:12][C:11]5[CH:14]=[C:15]6[C:19](=[CH:20][C:10]4=5)[CH2:18][CH2:17][O:16]6)[C:2]3=[O:21])=[CH:50][C:49]=2[CH:51]=[CH:52][CH:53]=1

Participants

5

Reactant 4

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 592633545,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-oneHCID 593524533-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3'-indol]-2'(1H)-oneHCID 67357394HCID 67357394, compound

Product 1

HCID 59352582HCID 59352582, compound

Procedure

Following the procedure as described in EXAMPLE 9 and making non-critical variations using 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1H)-one, and 2-(bromomethyl)-7-fluorobenzofuran to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, 1′-[(7-fluoro-1-benzofuran-2-yl)methyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one was obtained (83%) as a colorless solid: mp 192-193° C.; 1H NMR (300 MHz, CDCl3) δ7.31-7.24 (m, 2H), 7.22-6.96 (m, 5H), 6.77-6.74 (m, 1H), 6.56 (s, 1H), 6.43 (s, 1H), 5.31-5.23 (m, 1H), 5.03-4.95 (m, 2H), 4.75-4.68 (m, 1H), 4.59-4.49 (m, 2H), 3.10-2.91 (m, 2H); 13C NMR (75 MHz, CDCl3) δ177.6, 161.8, 161.2, 152.8, 147.8 (d, JC-F=249.7 Hz), 141.9 (d, JC-F=11.3 Hz), 141.4, 132.7, 131.6 (d, JC-F=3.2 Hz), 128.8, 123.9, 123.7, 123.6, 120.1 (d, JC-F=5.2 Hz), 119.0, 116.6 (d, JC-F=3.9 Hz), 110.8 (d, JC-F=16.1 Hz), 109.0, 105.6 (d, JC-F=2.1 Hz), 93.2, 80.4, 72.4, 57.7, 37.5, 29.0; MS (ES+) m/z 428.3 (M+1).

Sources & evidence

ORD record
ord-b9499cf825034ebc8abad7a3765e5f0a
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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