2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178487409, compound

HRID 2271797Notes

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]#[N:13])=[C:5]2[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([N:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]1.[Cl:24][C:25]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[C:27]([O:40][CH3:41])[C:26]=1[OH:42]>>[Cl:24][C:25]1[CH:30]=[C:29]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]3[NH:14][C@H:15]2[CH2:20][CH2:19][C@H:18]([N:21]([CH3:22])[CH3:23])[CH2:17][CH2:16]2)[CH:28]=[C:27]([O:40][CH3:41])[C:26]=1[OH:42]

Participants

Reactant 2

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

HCID 178484092HCID 178484092, compound

Product 1

HCID 178487409HCID 178487409, compoundYield 35.2%

Procedure

Following general procedure D, 6-bromo-4-((trans-4-(dimethylamino)cyclohexyl)amino)quinoline-3-carbonitrile (28 mg, 0.075 mmol) was reacted with 2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (32 mg, 0.113 mmol) to afford the desired product (11.9 mg, 35%) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 8.46-8.40 (m, 2H), 8.02 (dd, J=8.7, 1.9 Hz, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.42 (d, J=2.0 Hz, 1H), 7.29 (d, J=2.0 Hz, 1H), 4.48-4.38 (m, 1H), 3.99 (s, 3H), 2.50-2.39 (m, 1H), 2.35 (s, 6H), 2.29 (d, J=11.8 Hz, 2H), 2.06 (d, J=12.0 Hz, 2H), 1.73-1.61 (m, 2H), 1.59-1.47 (m, 2H). ESI MS m/z 451 [C25H27ClN4O2+H]+; HPLC 98.8% (AUC), tR=10.61 min.

Sources & evidence

ORD record: ord-c7db785178a24ef8bf36d0b96c239612
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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