(3-Amino-6-iodo-1-benzofuran-2-yl)(2,4-dichlorophenyl)methanone → (3-Amino-8-benzyl-5,6,7,8-tetrahydro-furo[3,2-g]quinolin-2-yl)-(2,4-dichloro-phenyl)methanone

HRID 131177Notes

Reaction equation

HRID 131177 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:19]#[N:20])=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1C2C=CC(I)=CC=2O[C:23]=1[C:32]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=1[Cl:41])=[O:33]>>[NH2:20][C:19]1[C:14]2[CH:13]=[C:12]3[C:17](=[CH:16][C:15]=2[O:18][C:23]=1[C:32]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=1[Cl:41])=[O:33])[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][CH2:10][CH2:11]3

Participants

3

Reactant 2

HCID 21864959(3-Amino-6-iodo-1-benzofuran-2-yl)(2,4-dichlorophenyl)methanoneHCID 218649691-Benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbonitrile

Product 1

HCID 21864954(3-Amino-8-benzyl-5,6,7,8-tetrahydro-furo[3,2-g]quinolin-2-yl)-(2,4-dichloro-phenyl)methanoneYield 29%

Procedure

This compound was prepared from 1-benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (20 mg, 0.08 mmol) from step 4 in the manner described for [(3-amino-6-iodo-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone, affording 10 mg (29%) of the title compound as a yellow solid. 1H-NMR (CDCl3) δ 7.44-7.40 (m, 2H), 7.33-7.22 (m, 4H), 7.18 (s, 1H), 7.15-7.13 (m, 2H), 6.25 (s, 1H), 5.96 (bs, 2H), 4.52 (s, 2H) 3.47 (t, J=6.0 Hz, 2H), 2.89 (t, J=5.9 Hz, 2H), 2.03 (m, 2H); MS LC-MS (MH+=451.3), LC MS RT: 3.81 min.

Sources & evidence

ORD record
ord-f7caac2e9bc84d958bb80a5c03e9d80d
Source dataset
uspto-grants-2008_06
Patent number
US07384947B2

Reaction notes

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