HCID 66715275, compound → HCID 68092008, compound

HRID 2271758Notes

Reaction equation

HRID 2271758 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]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)[CH2:19][CH2:18]1.[Cl:30][C:31]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[C:33]([F:46])[C:32]=1[OH:47]>>[Cl:30][C:31]1[CH:36]=[C:35]([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[CH2:15][CH2:16]2)=[O:13])=[C:5]3[N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)[CH2:19][CH2:18]2)[CH:34]=[C:33]([F:46])[C:32]=1[OH:47]

Participants

3

Reactant 2

HCID 66715275HCID 66715275, compoundHCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 68092008HCID 68092008, compoundYield 67%

Procedure

Following general procedure D, {6-bromo-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanone (30 mg, 0.066 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (41 mg, 0.150 mmol) to afford the desired product (23 mg, 67%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.77 (s, 1H), 8.28 (d, J=1.3 Hz, 1H), 8.05-7.99 (m, 2H), 7.58-7.53 (m, 1H), 7.46 (dd, J=11.6, 2.2 Hz, 1H), 3.55 (d, J=13.1 Hz, 2H), 3.25-3.15 (m, 2H), 2.93-2.47 (m, 10H), 2.39 (s, 3H), 2.12 (d, J=10.8 Hz, 2H), 1.96-1.82 (m, 2H), 1.34-1.28 (m, 2H), 1.27-1.20 (m, 2H); ESI MS m/z 523 [C29H32ClFN4O2+H]+; HPLC>99% (AUC), tR=10.14 min.

Sources & evidence

ORD record
ord-3e6edde5eb8b490b8ebde8402d11fa98
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…