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

HRID 1407777Notes

Reaction equation

HRID 1407777 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-ecf367c381ac4afab795e7b50d3a84e8
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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