1-(Bromomethyl)-2-(difluoromethyl)benzene → HCID 46194856, compound

HRID 1407758Notes

Reaction equation

HRID 1407758 reaction equation
N1[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[O:19][CH2:18][CH2:17][O:16][C:15]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=[O:22].N1C2C(=CC=CC=2)[C:25]2([C:35]3=[CH:36][C:37]4OCO[C:38]=4[CH:42]=[C:34]3O[CH2:32]2)C1=O.BrCC1C=CC=CC=1[CH:52]([F:54])[F:53].CC1C=CC(S(OC[C@H]2COCCO2)(=O)=O)=CC=1>>[F:53][CH:52]([F:54])[C:34]1[CH:42]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:25][CH:32]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[O:19][CH2:18][CH2:17][O:16][C:15]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=[O:22]

Participants

5

Reactant 4

HCID 226714721-(Bromomethyl)-2-(difluoromethyl)benzeneHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 58224164Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydroHCID 59253203(R)-(1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 46194856HCID 46194856, compound

Procedure

Following the procedure as described in EXAMPLE 8 and making non-critical variations using 2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and 1-(bromomethyl)-2-(difluoromethyl)benzene to replace (R)-(1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate, 3′-[2-(difluoromethyl)benzyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,1′-inden]-2′(3′H)-one was obtained (52%) as a colorless solid: mp 191-193° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.67 (d, J=7.4 Hz, 1H), 7.52-7.46 (m, 2H), 7.37 (s, 1H), 7.26-7.20 (m, 3H), 7.06 (dd, J=7.4, 7.4 Hz, 1H), 6.85 (d, J=7.8 Hz, 1H), 6.53 (s, 1H), 6.24 (s, 1H), 5.17-5.04 (m, 2H), 4.77 (ABq, 2H), 4.20-4.11 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 177.4, 155.3, 144.7, 142.6, 138.3, 134.5 (t, JC-F=3.8 Hz), 132.1, 131.9, 131.8 (t, JC-F=21.3 Hz), 129.3, 128.3, 127.4, 127.0 (t, JC-F=7.7 Hz), 124.3, 123.7, 121.5, 114.9 (t, JC-F=236.0 Hz), 111.8, 109.8, 99.3, 80.1, 64.7, 64.1, 57.8; MS (ES+) m/z 435.7 (M+1).

Sources & evidence

ORD record
ord-ed405a7692a84223bbb26bd895b6abb3
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…