2-(Bromomethyl)-5-(trifluoromethyl)furan → HCID 59352278, compound

HRID 1965645Notes

Reaction equation

HRID 1965645 reaction equation
[F:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:19][CH2:18][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:10][C:9]3=[O:17])[C:6]=2[CH:7]=1.CC1C2C=C3[C:33]4([C:41]5[C:36](=CC=[CH:39][CH:40]=5)[NH:35][C:34]4=O)COC3=CC=2ON=1.Br.BrCC1C=NC=CC=1.BrCC1OC(C(F)(F)F)=CC=1>>[F:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:19][CH2:18][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:33][C:41]4[CH:36]=[N:35][CH:34]=[CH:39][CH:40]=4)[C:9]3=[O:17])[C:6]=2[CH:7]=1

Participants

5

Reactant 4

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 593524533-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3'-indol]-2'(1H)-oneHCID 593525695,6-difluorospiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 59352278HCID 59352278, compound

Procedure

Following the procedure as described in EXAMPLE 9 and making non-critical variations using 5,6-difluorospiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, and 3-(bromomethyl)pyridine hydrobromide to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, 5,6-difluoro-1′-(pyridin-3-ylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (57%) as a colorless solid: mp 175-177° C.; 1H NMR (300 MHz, CD3OD) δ 8.98 (s, 1H), 8.84 (d, J=5.4 Hz, 1H), 8.67 (d, J=8.4 Hz, 1H), 8.12 (dd, J=8.1, 6.0 Hz, 1H), 7.37 (ddd, J=7.5, 7.5, 1.2 Hz, 1H), 7.26 (d, J=6.9 Hz, 1H), 7.18 (d, J=7.8 Hz, 1H), 7.15 (d, J=7.8 Hz, 1H), 6.93 (dd, J=10.5, 6.3 Hz, 1H), 6.76 (dd, J=9.6, 7.8 Hz, 1H), 5.27 (s, 1H), 5.26 (s, 1H), 5.00 (d, J=9.6 Hz, 1H), 4.83 (d, J=9.6 Hz, 1H); MS (ES+) m/z 365.2 (M+1).

Sources & evidence

ORD record
ord-065c1ff3fb404f48a161463c62a5c05b
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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