{6-Bromo-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanone → Cyclopropyl {6-(3-fluoro-4-hydroxy-5-methoxyphenyl)-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}methanone

HRID 2271750Notes

Reaction equation

HRID 2271750 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.[F:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[C:32]([O:45][CH3:46])[C:31]=1[OH:47]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:19][CH2:18]2)=[CH:3][C:2]([C:34]2[CH:33]=[C:32]([O:45][CH3:46])[C:31]([OH:47])=[C:30]([F:29])[CH:35]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 66715460{6-Bromo-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanoneHCID 866929282-Fluoro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 66715519Cyclopropyl {6-(3-fluoro-4-hydroxy-5-methoxyphenyl)-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}methanoneYield 52%

Procedure

Following general procedure D, {6-bromo-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanone (26 mg, 0.059 mmol) was reacted with 2-fluoro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (32 mg, 0.118 mmol) to afford the desired product (15.4 mg, 52%) as a gray solid: 1H NMR (500 MHz, CD3OD) δ 8.78 (s, 1H), 8.27 (s, 1H), 8.03 (s, 2H), 7.23-7.04 (m, 2H), 3.99 (s, 3H), 3.54 (d, J=12.8 Hz, 2H), 3.28-3.11 (m, 6H), 3.05 (d, J=6.6 Hz, 2H), 2.63-2.51 (m, 1H), 2.20-1.89 (m, 7H), 1.80-1.58 (m, 2H), 1.41-1.16 (m, 4H).

Sources & evidence

ORD record
ord-32cfb309471347c4ac03cd15aeeae80f
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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