2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Cyclopropyl{6-(3,5-dichloro-4-hydroxyphenyl)-4-[5-(2-(pyrrolidin-1-yl)ethyl)pyridin-3-ylamino]quinolin-3-yl}methanone

HRID 2271973Notes

Reaction equation

HRID 2271973 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[NH:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:23]=1.[Cl:31][C:32]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[C:34]([Cl:47])[C:33]=1[OH:48]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[NH:17][C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH2:24][CH2:25][N:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)[CH:23]=2)=[CH:3][C:2]([C:36]2[CH:37]=[C:32]([Cl:31])[C:33]([OH:48])=[C:34]([Cl:47])[CH:35]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 86692896{6-Bromo-4-[5-(2-(pyrrolidin-1-yl)ethyl)pyridin-3-ylamino]quinolin-3-yl}(cyclopropyl)methanone

Product 1

HCID 66716005Cyclopropyl{6-(3,5-dichloro-4-hydroxyphenyl)-4-[5-(2-(pyrrolidin-1-yl)ethyl)pyridin-3-ylamino]quinolin-3-yl}methanoneYield 46%

Procedure

Following general procedure A-1, {6-bromo-4-[5-(2-(pyrrolidin-1-yl)ethyl)pyridin-3-ylamino]quinolin-3-yl}(cyclopropyl)methanone (54 mg, 0.116 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (50 mg, 0.174 mmol) to afford the desired product (29 mg, 46%) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.36 (s, 1H), 8.64 (dd, J=16.9, 2.1 Hz, 2H), 8.32 (dd, J=8.8, 2.0 Hz, 1H), 8.17 (d, J=2.0 Hz, 1H), 8.11 (d, J=8.8 Hz, 1H), 7.99 (t, J=2.0 Hz, 1H), 7.43 (s, 2H), 3.74-3.70 (m, 2H), 3.50-3.43 (m, 2H), 3.24-3.17 (m, 2H), 3.16-3.12 (m, 2H), 2.79-2.76 (m, 1H), 2.19-2.15 (m, 2H), 2.07-2.03 (m, 2H), 1.18-1.07 (m, 4H); ESI MS m/z 547 [C30H28Cl2N4O2+H]+; HPLC>99% (AUC), tR=9.93 min.

Sources & evidence

ORD record
ord-36ac6e98cf734a8cb3464b8cace70005
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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