Acetone → HCID 46195425, compound

HRID 1407672Notes

Reaction equation

HRID 1407672 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:18]3[C:13](=[CH:14][C:15]4[O:21][CH2:20][CH2:19][C:16]=4[CH:17]=3)[O:12][CH2:11][CH2:10]2)[C:2]1=[O:22].CC(C)=O.Br[CH2:28][C:29]1[O:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:33]=1.BrCC1CCCCO1>CC(=O)CC>[F:35][C:34]([F:37])([F:36])[C:31]1[O:30][C:29]([CH2:28][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]3([C:18]4[C:13](=[CH:14][C:15]5[O:21][CH2:20][CH2:19][C:16]=5[CH:17]=4)[O:12][CH2:11][CH2:10]3)[C:2]2=[O:22])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 46195282HCID 46195282, compound

Product 1

HCID 46195425HCID 46195425, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using 2,3,6,7-tetrahydrospiro[furo[3,2-g]chromene-5,3′-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, acetone to replace butanone, and 2-(bromomethyl)-5-(trifluoromethyl)furan to replace 2-(bromomethyl)tetrahydro-2H-pyran, 1′-{[5-(trifluoromethyl)furan-2-yl]methyl}-2,3,6,7-tetrahydrospiro[furo[3,2-g]chromene-5,3′-indol]-2′(1′H)-one was obtained (43%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ7.36-6.93 (m, 4H), 6.76-6.70 (m, 1H), 6.38 (d, J=3.5 Hz, 1H), 6.36 (s, 1H), 6.21 (s, 1H), 4.98 (ABq, 2H), 4.80-4.69 (m, 1H), 4.45 (t, J=8.6 Hz, 2H), 4.36-4.28 (m, 1H), 2.92 (t, J=8.5 Hz, 2H), 2.23-2.16 (m, 2H); 13C NMR (75 MHz, CDCl3) δ179.3, 160.6, 155.5, 152.2, 152.1, 141.8, 141.6, 141.3, 135.2, 128.3, 124.1, 123.5, 123.5, 120.6, 120.4, 117.0, 112.6 (2C), 112.5 (2C), 112.1, 109.1, 108.6, 98.6, 71.8, 62.0, 47.8, 36.7, 32.4, 28.8; MS (ES+) m/z 441.7 (M+1).

Sources & evidence

ORD record
ord-a79b2fbba8534c89b20f871a14e074f3
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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