2-(Bromomethyl)tetrahydro-2H-pyran → HCID 59352759, compound

HRID 1407693Notes

Reaction equation

HRID 1407693 reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.BrCC1CCCCO1.[O:18]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2[C:33]2([C:52]4[C:43](=[CH:44][C:45]5[O:50][CH2:49][CH2:48][O:47][C:46]=5[CH:51]=4)[O:42][CH2:41]2)[C:34](=[O:40])[NH:35]3)=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[O:18]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2[C:33]2([C:52]4[C:43](=[CH:44][C:45]5[O:50][CH2:49][CH2:48][O:47][C:46]=5[CH:51]=4)[O:42][CH2:41]2)[C:34](=[O:40])[N:35]3[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 59352216HCID 59352216, compound

Product 1

HCID 59352759HCID 59352759, compound

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using 2-(bromomethyl)pyridine hydrobromide to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 4′-(4-phenoxyphenyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 4′-(4-phenoxyphenyl)-1′-(pyridin-2-ylmethyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (90%) as a colorless solid: mp 196-199° C. (dichloromethane/ether); 1H NMR (300 MHz, CDCl3) δ 8.61-8.57 (m, 1H), 7.69-7.65 (m, 1H), 7.40-7.18 (m, 5H), 7.12-7.05 (m, 1H), 7.02-6.97 (m, 2H), 6.93-6.86 (m, 2H), 6.84-6.71 (m, 4H), 6.39 (s, 1H), 6.21 (s, 1H), 5.26 (d, J=15.8 Hz, 1H), 4.95 (d, J=15.8 Hz, 1H), 4.73 (d, J=9.0 Hz, 1H), 4.43 (d, J=9.0 Hz, 1H), 4.20-4.07 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 178.2, 157.4, 156.3, 155.6, 149.6, 144.7, 142.4, 139.8, 137.9, 137.1, 133.5, 130.4, 130.1, 129.7, 128.7, 125.4, 123.1, 122.8, 122.3, 121.7, 118.6, 118.4, 111.2, 108.7, 99.3, 77.9, 64.5, 64.0, 58.5, 46.2; MS (ES+) m/z 555.0 (M+1).

Sources & evidence

ORD record
ord-495eec1cc33f4f13af6f01078a433197
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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