tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate → tert-Butyl 4-(((4-(4-amino-2-fluorophenoxy)-6-methoxyquinolin-7-yl)oxy)methyl)piperidine-1-carboxylate

HRID 1465205Notes

Reaction equation

HRID 1465205 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.Br[CH2:26][CH:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1>>[NH2:22][C:20]1[CH:19]=[CH:18][C:3]([O:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:17][CH2:26][CH:27]4[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[CH2:29][CH2:28]4)=[C:12]([O:15][CH3:16])[CH:13]=3)[N:8]=[CH:7][CH:6]=2)=[C:2]([F:1])[CH:21]=1

Participants

3

Reactant 2

HCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 1361757014-(2-Fluoro-4-nitrophenoxy)-7-hydroxy-6-methoxyquinoline

Product 1

HCID 59342474tert-Butyl 4-(((4-(4-amino-2-fluorophenoxy)-6-methoxyquinolin-7-yl)oxy)methyl)piperidine-1-carboxylate

Procedure

U1 was prepared from 4-(2-fluoro-4-nitro-phenoxy)-6-methoxy-quinolin-7-ol and tert-butyl 4-(bromomethyl)piperidine-1-carboxylate following the general procedure reported in Preparative Example 54 Step 1-2. 1H NMR (400 MHz, CDCl3, 300K) δ 1.22 (m, 2H), 1.40 (s, 9H), 1.82 (d, J=12.7 Hz, 2H), 2.10 (m, 1H), 2.69 (t, J=12.3 Hz, 2H), 3.77 (m, 2H), 3.96 (s, 3H), 3.97 (m, 2H), 4.10 (m, 2H), 6.31 (d, J=5.2 Hz, 1H), 6.46 (m, 2H), 6.96 (t, J=8.7 Hz, 1H), 7.31 (s, 1H), 7.51 (s, 1H), 8.40 (d, J=5.2 Hz, 1H). MS (ES) C27H32FN3O5 requires: 497. Found: 498 (M+H)+.

Sources & evidence

ORD record
ord-703d4eb399194cc996002a2bdb4d74ec
Source dataset
uspto-grants-2015_04
Patent number
US08999982B2

Reaction notes

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