9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 67450756, compound

HRID 1853774Notes

Reaction equation

HRID 1853774 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].[F:18][C:19]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[CH:28][C:20]=1[CH2:21][N:22]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]1>>[F:18][C:19]1[CH: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][C:20]=1[CH2:21][N:22]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]1

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 67453252HCID 67453252, compound

Product 1

HCID 67450756HCID 67450756, compoundYield 52.8%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (180 mg, 0.58 mmol) was reacted with 1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]pyrrolidin-3-ol (280 mg, 0.87 mmol) to afford the desired product (130 mg, 48%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.79-7.72 (m, 1H), 7.66 (d, J=5.4 Hz, 1H), 7.58 (d, J=9.1 Hz, 1H), 7.42 (d, J=9.1 Hz, 1H), 7.33-7.21 (m, 2H), 6.09 (td, J=5.3, 2.4 Hz, 1H), 4.75-4.53 (m, 3H), 3.91-3.66 (m, 4H), 3.66-3.34 (m, 3H), 2.55-2.44 (m, 1H), 2.28-2.15 (m, 1H), 2.14-2.04 (m, 1H).

Sources & evidence

ORD record
ord-5c1396c732fa499485cc5b37e15e3b82
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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