2-(Bromomethyl)-5-(trifluoromethyl)furan → HCID 59352220, compound

HRID 2385375Notes

Reaction equation

HRID 2385375 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=2

Participants

5

Reactant 4

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 46195570HCID 46195570, compoundHCID 593524533-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3'-indol]-2'(1H)-one

Product 1

HCID 59352220HCID 59352220, compound

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-4bda5d1b06e840f8b368a18a5cb67ac8
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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