(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate → 4'-fluoro-7'-methyl-1'-[(2R)-tetrahydrofuran-2-ylmethyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1H)-one

HRID 1965613Notes

Reaction equation

HRID 1965613 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4]1([CH2:16][O:15][C:14]3[CH:17]=[C:18]4[C:22](=[CH:23][C:13]1=3)[CH2:21][CH2:20][O:19]4)[C:5](=[O:12])[NH:6]2.N1C2C(=CC=CC=2)[C:26]2([C:36]3=CC4OCOC=4[CH:43]=[C:35]3[O:34][CH2:33]2)C1=O.CC1C=CC(S(OC[C@H]2CCCO2)(=O)=O)=CC=1.CC1C=CC(S(OC[C@H]2COCCO2)(=O)=O)=CC=1>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4]1([CH2:16][O:15][C:14]3[CH:17]=[C:18]4[C:22](=[CH:23][C:13]1=3)[CH2:21][CH2:20][O:19]4)[C:5](=[O:12])[N:6]2[CH2:43][C@H:35]1[CH2:36][CH2:26][CH2:33][O:34]1

Participants

5

Reactant 4

HCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 59253203(R)-(1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonateHCID 593521314'-fluoro-7'-methyl-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 686001324'-fluoro-7'-methyl-1'-[(2R)-tetrahydrofuran-2-ylmethyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1H)-one

Procedure

Following the procedure as described in EXAMPLE 8 and making non-critical variations using 4′-fluoro-7′-methyl-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one to replace spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate to replace (R)-(1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate, 4′-fluoro-7′-methyl-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1H)-one was obtained (76%) as a colorless solid: mp 175-176° C. (diethyl ether); 1H NMR (300 MHz, CD3OD) δ7.14-7.06 (m, 1H), 6.71-6.52 (m, 2H), 6.25 (d, J=2.3 Hz, 1H), 4.80-4.78 (m, 2H), 4.51 (t, J=8.6 Hz, 2H), 4.26-3.69 (m, 5H), 3.00 (t, J=8.6 Hz, 2H), 2.56 (s, 3H), 2.16-1.87 (m, 3H), 1.78-1.69 (m, 1H); MS (ES+) m/z 396.0 (M+1).

Sources & evidence

ORD record
ord-7fa46ed2b58248219951fcf9b155ede9
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

Loading…