2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 86692934, compound

HRID 2271778Notes

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](=[O:14])[CH3:13])=[C:5]2[N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:17][CH2:16]1.[Cl:27][C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[C:30]([O:43][CH3:44])[C:29]=1[OH:45]>>[Cl:27][C:28]1[CH:33]=[C:32]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[N:15]2[CH2:16][CH2:17][CH:18]([CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:19][CH2:20]2)[CH:31]=[C:30]([O:43][CH3:44])[C:29]=1[OH:45]

Participants

Reactant 2

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

HCID 66715820HCID 66715820, compound

Product 1

HCID 86692934HCID 86692934, compoundYield 71.4%

Procedure

Following general procedure D, 1-{6-bromo-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}ethanone (30 mg, 0.072 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 (25.4 mg, 71%) as a yellow brown solid: 1H NMR (500 MHz, CD3OD) δ 8.80 (s, 1H), 8.29 (s, 1H), 8.03 (s, 2H), 7.30 (d, J=2.1 Hz, 1H), 7.24 (d, J=2.0 Hz, 1H), 3.99 (s, 3H), 3.49 (d, J=12.9 Hz, 2H), 3.24-3.12 (m, 6H), 3.02 (d, J=5.5 Hz, 2H), 2.70 (s, 3H), 2.13-1.96 (m, 7H), 1.77-1.62 (m, 2H); ESI MS m/z 494 [C28H32ClN3O3+H]+; HPLC>99% (AUC), tR=10.45 min.

Sources & evidence

ORD record: ord-99ac654ce644483a93303a0f390bd909
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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