2-(Bromomethyl)tetrahydro-2H-pyran → HCID 59352235, compound

HRID 2385284Notes

Reaction equation

HRID 2385284 reaction equation
Cl.Cl[CH2:3][C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][N:5]=1.BrCC1CCCCO1.[CH3:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:32])[C:26]12[C:44]2[C:35](=[CH:36][C:37]3[O:42][CH2:41][CH2:40][O:39][C:38]=3[CH:43]=2)[O:34][CH2:33]1.N1C2C(=CC=CC=2)C2(COC3C=C4C(=CC2=3)CCO4)C1=O>>[CH3:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH2:3][C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][N:5]=1)[C:27](=[O:32])[C:26]12[C:44]2[C:35](=[CH:36][C:37]3[O:42][CH2:41][CH2:40][O:39][C:38]=3[CH:43]=2)[O:34][CH2:33]1

Participants

5

Reactant 4

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 592633545,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-oneHCID 593526605'-methyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1H)-oneHCID 667065662-(Chloromethyl)-3-(trifluoromethyl)pyridine hydrochloride

Product 1

HCID 59352235HCID 59352235, compound

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using 2-(chloromethyl)-3-(trifluoromethyl)pyridine hydrochloride to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 5′-methyl-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, (5′-methyl-1′-{[3-(trifluoromethyl)pyridin-2-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]-benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (62%) as a colorless solid: mp 137-139° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 8.63 (d, J=4.6 Hz, 1H), 8.22 (d, J=7.5 Hz, 1H), 7.57-7.50 (m, 1H), 7.02-6.94 (m, 2H), 6.72 (d, J=7.9 Hz, 1H), 6.47 (s, 1H), 6.40 (s, 1H), 5.29-5.03 (ABq, 2H), 4.76-4.64 (ABq, 2H), 4.18-4.06 (m, 4H), 2.18 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 177.4, 155.0, 153.0, 152.9, 144.5, 140.9, 138.2, 135.5 (q, 4J=5.31 Hz), 132.5, 132.5, 129.3, 124.5, 124.4 (q, 1J=273.6 Hz), 123.5 (q, 2J=32.3 Hz), 123.5, 122.2, 112.3, 109.3, 99.1, 79.7, 64.7, 64.1, 57.8, 42.4 (q, J=3.1 Hz), 21.0; MS (ES+) m/z 469.0 (M+1).

Sources & evidence

ORD record
ord-8014e11122884ad885c9bb646ec18e85
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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