2-(Bromomethyl)pyridine hydrobromide → HCID 59352657, compound

HRID 1965588Notes

Reaction equation

HRID 1965588 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:21]3[C:12](=[CH:13][C:14]4[CH2:15][CH2:16][CH2:17][O:18][C:19]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=[O:22].FC1C2OCCOC=2C=C2OCC3(C4C(=CC=CC=4)NC3=O)C=12.Cl.Cl[CH2:48][C:49]1[C:54]([C:55]([F:58])([F:57])[F:56])=[CH:53][CH:52]=[CH:51][N:50]=1.Br.BrCC1C=CC=CN=1>>[F:58][C:55]([F:56])([F:57])[C:54]1[C:49]([CH2:48][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]3([C:21]4[C:12](=[CH:13][C:14]5[CH2:15][CH2:16][CH2:17][O:18][C:19]=5[CH:20]=4)[O:11][CH2:10]3)[C:2]2=[O:22])=[N:50][CH:51]=[CH:52][CH:53]=1

Participants

5

Reactant 4

HCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 593524357,8-dihydro-6H-spiro[furo[2,3-g]chromene-3,3'-indol]-2'(1'H)-oneHCID 593527429-fluoro-2,3-dihydro-spiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-oneHCID 667065662-(Chloromethyl)-3-(trifluoromethyl)pyridine hydrochloride

Product 1

HCID 59352657HCID 59352657, compound

Procedure

Following the procedure as described in EXAMPLE 5.25 and making non-critical variations using 7,8-dihydro-6H-spiro[furo[2,3-g]chromene-3,3′-indol]-2′(1H)-one to replace 9-fluoro-2,3-dihydro-spiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one, and 2-(chloromethyl)-3-(trifluoromethyl)pyridine hydrochloride to replace 2-(bromomethyl)pyridine hydrobromide, 1′-{[3-(trifluoromethyl)pyridin-2-yl]methyl}-7,8-dihydro-6H-spiro[furo[2,3-g]chromene-3,3′-indol]-2′(1′H)-one was obtained (2%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 8.65 (d, J=4.4 Hz, 1H), 8.25 (d, J=7.8 Hz, 1H), 7.56 (dd, J=7.8, 5.0 Hz, 1H), 7.20-7.26 (m, 1H), 7.15 (d, J=6.9 Hz, 1H), 7.01 (t, J=7.4 Hz, 1H), 6.88 (d, J=7.8 Hz, 1H), 6.65 (s, 1H), 6.31 (s, 1H), 5.22 (ABq, J=39.2 Hz, 2H), 4.72 (ABq, J=18.8 Hz, 2H), 4.04-3.95 (m, 2H), 2.70 (t, J=6.4 Hz, 2H), 1.89-1.77 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ177.1, 155.7, 154.3, 149.7, 149.4, 143.0, 137.5, 132.3, 129.1, 128.6, 123.9, 123.6, 123.4, 123.1, 122.0, 111.5, 110.4, 109.8, 79.3, 66.2, 58.0, 45.2, 25.2, 22.1; MS (ES+) m/z 453.2 (M+1).

Sources & evidence

ORD record
ord-0f9b413f886848cfb933dc2733cdf931
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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