{6-Bromo-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanone → Cyclopropyl{6-[4-hydroxy-3-(trifluoromethoxy)phenyl]-4-[4-(pyrrolidin-1-ylmethyl]piperidin-1-yl}quinolin-3-yl)methanone

HRID 2271751Notes

Reaction equation

HRID 2271751 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:19][CH2:18]1.CC1(C)C(C)(C)OB([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([O:44][C:45]([F:48])([F:47])[F:46])[CH:38]=2)O1>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][N:24]4[CH2:25][CH2:26][CH2:27][CH2:28]4)[CH2:21][CH2:22]2)=[CH:3][C:2]([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([O:44][C:45]([F:46])([F:48])[F:47])[CH:38]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 66715460{6-Bromo-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanoneHCID 747894824-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethoxy)phenol

Product 1

HCID 66715528Cyclopropyl{6-[4-hydroxy-3-(trifluoromethoxy)phenyl]-4-[4-(pyrrolidin-1-ylmethyl]piperidin-1-yl}quinolin-3-yl)methanone

Procedure

Following general procedure D, {6-bromo-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanone (30 mg, 0.068 mmol) was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethoxy)phenol (36 mg, 0.140 mmol) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.80 (s, 1H), 8.28 (d, J=1.6 Hz, 1H), 8.08-7.98 (m, 2H), 7.64-7.57 (m, 2H), 7.12 (d, J=9.0 Hz, 1H), 3.54 (d, J=12.8 Hz, 2H), 3.22 (t, J=11.5 Hz, 2H), 3.13 (s, 4H), 2.99 (s, 2H), 2.64-2.50 (m, 1H), 2.10-1.92 (m, 7H), 1.74-1.59 (m, 2H), 1.36-1.28 (m, 2H), 1.28-1.19 (m, 2H); ESI MS m/z 540 [C30H32F3N3O3+H]+; HPLC>99% (AUC), tR=11.16 min.

Sources & evidence

ORD record
ord-2b23cc31a2864a2b9b8baee3e74b2a64
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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