2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178487412, compound

HRID 2271757Notes

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

Participants

Reactant 2

HCID 177502302-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

HCID 178519796HCID 178519796, compound

Product 1

HCID 178487412HCID 178487412, compoundYield 67%

Procedure

Following general procedure D, {6-bromo-4-[trans-4-(pyrrolidin-1-yl)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone (25 mg, 0.150 mmol) was reacted with 2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (43 mg, 0.150 mmol) to afford the desired product (20 mg, 67%), as a yellow-brown solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.34 (d, J=1.9 Hz, 1H), 8.03 (dd, J=8.7, 1.9 Hz, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.29 (d, J=2.1 Hz, 1H), 7.22 (d, J=2.0 Hz, 1H), 4.15 (t, J=10.6 Hz, 1H), 3.99 (s, 3H), 3.16 (s, 4H), 2.94 (s, 1H), 2.89-2.79 (m, 1H), 2.38 (d, J=12.5 Hz, 2H), 2.28 (d, J=11.9 Hz, 2H), 1.99 (s, 4H), 1.70-1.50 (m, 4H), 1.23-1.17 (m, 2H), 1.13-1.06 (m, 2H); ESI MS m/z 520 [C30H34ClN3O3+H]+; HPLC 98.7% (AUC), tR=10.99 min.

Sources & evidence

ORD record: ord-a3d6acbadadf482f9588e521c535d211
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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