2-(Bromomethyl)-5-(trifluoromethyl)furan → HCID 59352746, compound

HRID 1407785Notes

Reaction equation

HRID 1407785 reaction equation
CC1[C:6]2[CH:7]=[C:8]3[C:13]4([C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[NH:15][C:14]4=[O:22])[CH2:12][O:11][C:9]3=[CH:10][C:5]=2[O:4]N=1.[C:23]([O:27][C:28](=[O:38])[NH:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Br)=[CH:32][N:31]=1)([CH3:26])([CH3:25])[CH3:24].Br[CH2:40][C:41]1[O:42]C(C(F)(F)F)=CC=1>>[O:22]=[C:14]1[C:13]2([C:8]3[C:9](=[CH:10][C:5]4[O:4][CH2:40][CH2:41][O:42][C:6]=4[CH:7]=3)[O:11][CH2:12]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]1[CH2:36][C:33]1[CH:34]=[CH:35][C:30]([NH:29][C:28](=[O:38])[O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:31][CH:32]=1

Participants

4

Reactant 3

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamateHCID 593524533-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3'-indol]-2'(1H)-one

Product 1

HCID 59352746HCID 59352746, compound

Procedure

Following the procedure as described in EXAMPLE 9 and making non-critical variations using 2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3-indol]-2′(1′H)-one to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, and tert-butyl[5-(bromomethyl)pyridin-2-yl]carbamate to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, tert-butyl {5-[(2′-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-1′(2′H)-yl)methyl]pyridin-2-yl}carbamate was obtained (74%) as a colorless solid: mp 238-239° C.; 1H NMR (300 MHz, DMSO-d6) δ9.81 (s, 1H), 8.30-8.27 (m, 1H), 7.79-7.73 (m, 1H), 7.73-7.66 (m, 1H), 7.31-7.24 (m, 1H), 7.20-7.14 (m, 1H), 7.12-6.99 (m, 2H), 6.52 (s, 1H), 6.06 (s, 1H), 4.89 (ABq, J=22.9, 15.5 Hz, 2H), 4.74 (ABq, J=44.4, 9.3 Hz, 2H), 4.23-4.05 (m, 4H), 1.45 (s, 9H); 13C NMR (75 MHz, DMSO-d6) δ 176.7, 154.6, 152.6, 151.8, 146.9, 144.1, 141.8, 137.8, 137.2, 131.6, 128.7, 126.2, 123.6, 123.1, 121.1, 112.2, 110.8, 109.3, 98.8, 79.5, 79.3, 64.1, 63.5, 57.2, 27.9; MS (ES+) m/z 502.1 (M+1).

Sources & evidence

ORD record
ord-bcf3c8b504794f3cafd5d251cf5b8f5b
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…