2-(Bromomethyl)tetrahydro-2H-pyran → 1'-(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-6-carbonitrile

HRID 1965554Notes

Reaction equation

HRID 1965554 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[O:7][CH2:8][CH2:9][O:10][C:5]=2[CH:4]=1.BrCC1CCCCO1.[O:21]=[C:22]1[C:30]2([C:34]3[CH:35]=[CH:36][C:37]([C:39]#[N:40])=[CH:38][C:33]=3[O:32][CH2:31]2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]1CC1C=CC=CN=1>>[O:7]1[C:6]2[CH:11]=[CH:12][C:3]([CH2:2][N:23]3[C:24]4[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:30]4([C:34]5[CH:35]=[CH:36][C:37]([C:39]#[N:40])=[CH:38][C:33]=5[O:32][CH2:31]4)[C:22]3=[O:21])=[CH:4][C:5]=2[O:10][CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 52302876-(Chloromethyl)-2,3-dihydro-1,4-benzodioxineHCID 593524152'-Oxo-1'-(pyridin-2-ylmethyl)-1',2'-dihydrospiro[1-benzofuran-3,3-indole]-6-carbonitrile

Product 1

HCID 593525601'-(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-6-carbonitrile

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using 6-(chloromethyl)-2,3-dihydrobenzo[b][1,4]dioxine (Capilla, A. S. et al., Tetrahedron (2001), 57:8297) to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 2′-oxo-1′-(pyridin-2-ylmethyl)-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-6-carbonitrile to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 1′-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-6-carbonitrile was obtained (54%) as a colorless solid: mp 181-183° C. (dichloromethane/diethyl ether); 1H NMR (300 MHz, CDCl3) δ 7.29-7.16 (m, 1H), 7.15-6.97 (m, 3H), 6.89-6.75 (m, 5H), 5.04 (d, J=9.2 Hz, 1H), 4.94 (d, J=15.3 Hz, 1H), 4.80-4.67 (m, 2H), 4.25-4.19 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 176.2, 160.8, 143.8, 143.3, 142.2, 134.7, 131.3, 129.5, 128.5, 125.8, 124.4, 123.8, 123.7, 120.5, 118.5, 117.8, 116.3, 113.8, 113.3, 109.8, 80.2, 64.3 (2C), 57.8, 43.8.

Sources & evidence

ORD record
ord-51b2fa2b2c41426eb2758bcf6b4e7910
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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