(5-{[(tert-Butoxycarbonyl)amino]methyl}thiophen-2-yl)boronic acid → HCID 89682167, compound

HRID 1853797Notes

Reaction equation

HRID 1853797 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].[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[S:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>>[C:18]([O:22][C:23](=[O:24])[NH:25][CH2:26][C:27]1[S:31][C:30]([C:2]2[C:3]3[C:4]4[CH:17]=[CH:16][S:15][C:5]=4[C:6](=[O:14])[NH:7][C:8]=3[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])=[CH:29][CH:28]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 46738981(5-{[(tert-Butoxycarbonyl)amino]methyl}thiophen-2-yl)boronic acidHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 89682167HCID 89682167, compoundYield 18%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 5-[(tert-butoxycarbonylamino)methyl]thiophen-2-ylboronic acid (130 mg, 0.53 mmol) to afford the desired product (30 mg, 18%) as a off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.74 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.1 Hz, 1H), 7.36 (d, J=9.1 Hz, 1H), 6.49 (d, J=3.1 Hz, 1H), 6.40 (br s, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.27 (s, 2H), 3.82 (s, 3H), 1.39 (s, 9H).

Sources & evidence

ORD record
ord-fbfeb74d8b0a4f22a9e76b0671e11bc1
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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