2-(Bromomethyl)-5-(trifluoromethyl)furan → HCID 59352220, compound
Reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[C:9]3[O:23][CH2:22][C:12]4([C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[NH:14][C:13]4=[O:21])[C:10]3=[CH:11][C:6]=2[O:5][CH2:4][C:3]1=[O:24].CC1C2C=[C:32]3[C:37]4(C5C(=CC=CC=5)NC4=O)[CH2:36][O:35][C:33]3=[CH:34]C=2ON=1.CC1C=CC(S(OC[C@H]2CCCO2)(=O)=O)=CC=1.BrCC1OC(C(F)(F)F)=CC=1>>[CH3:1][N:2]1[C:3](=[O:24])[CH2:4][O:5][C:6]2[CH:11]=[C:10]3[C:12]4([C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]([CH2:34][C@H:33]5[CH2:32][CH2:37][CH2:36][O:35]5)[C:13]4=[O:21])[CH2:22][O:23][C:9]3=[CH:8][C:7]1=2Participants
Procedure
Following the procedure as described in EXAMPLE 9 and making non-critical variations using 4-methyl-2H-spiro[furo[2,3-g][1,4]benzoxazine-8,3′-indole]-2′,3(1′H,4H)-dione to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, and (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, 4-methyl-1′-(((R)-tetrahydrofuran-2-yl)methyl)-4,7-dihydrospiro[benzofuro[5,6-b][1,4]oxazine-8,3′-indoline]-2′,3(2H)-dione was obtained (11%) as a colorless solid: 1H NMR (300 MHz, (CD3)2CO) δ7.35-7.30 (m, 1H), 7.23-7.13 (m, 2H), 7.08-6.99 (m, 1H), 6.75 (s, 1H), 6.35 (d, J=10.1 Hz, 1H), 4.92-4.87 (m, 1H), 4.74 (d, J=9.2 Hz, 1H), 4.45-4.44 (m, 2H), 4.31-4.20 (m, 1H), 3.97-3.62 (m, 4H), 3.33 (s, 3H), 1.95-1.66 (m, 4H); 13C NMR (75 MHz, (CD3)2CO) δ178.8, 178.7, 166.1, 158.4 (2C), 145.3, 145.1, 141.5, 133.9, 133.7, 133.2, 130.6, 130.5, 125.6, 125.3 (2C), 125.1 (2C), 124.6, 124.3, 112.9, 112.7, 111.6, 111.5, 99.2, 99.1, 82.0, 81.8 (2C), 79.6, 78.2, 77.9, 75.7, 69.4, 69.3, 69.1, 59.6, 59.5, 46.0, 45.8, 30.7, 30.4, 29.8, 29.4, 27.2, 27.1; MS (ES+) m/z 406.9 (M+1).
Sources & evidence
- ORD record
- ord-1520751ee825439d9c40655085b2caf4
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
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