(4-[1-(1-Piperidinyl)Ethyl]Phenyl)Boronic Acid → HCID 68229941, compound

HRID 1853765Notes

Reaction equation

HRID 1853765 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH:17]=[CH:16][S:15][C:5]=3[C:6](=[O:14])[NH:7][C:8]=2[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[N:18]1([CH:24]([C:26]2[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=2)[CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]2[NH:7][C:6](=[O:14])[C:5]3[S:15][CH:16]=[CH:17][C:4]=3[C:3]=2[C:2]=1[C:29]1[CH:28]=[CH:27][C:26]([CH:24]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:25])=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 45791104(4-[1-(1-Piperidinyl)Ethyl]Phenyl)Boronic AcidHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 68229941HCID 68229941, compoundYield 5%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 4-[1-(piperidin-1-yl)ethyl]phenylboronic acid (170 mg, 0.73 mmol) to afford the desired product (10 mg, 5%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.74-7.66 (m, 2H), 7.62-7.53 (m, 2H), 7.49-7.34 (m, 3H), 5.94 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 3.86-3.78 (m, 1H), 3.76 (s, 1H), 3.47 (d, J=12.6 Hz, 1H), 3.10-2.98 (m, 1H), 2.96-2.82 (m, 1H), 2.11-1.91 (m, 2H), 1.89 (d, J=7.0 Hz, 2H), 1.85-1.70 (m, 1H).

Sources & evidence

ORD record
ord-3aa0500149014fb99af44ff014dce195
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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