(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid → HCID 71737064, compound

HRID 2172328Notes

Reaction equation

HRID 2172328 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1B(O)O.Cl[C:17]1[N:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][N:21]([S:27]([NH:30][C:31]1[S:35][N:34]=[CH:33][N:32]=1)(=[O:29])=[O:28])[CH2:22]2>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:17]1[N:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][N:21]([S:27]([NH:30][C:31]1[S:35][N:34]=[CH:33][N:32]=1)(=[O:29])=[O:28])[CH2:22]2

Participants

3

Reactant 2

HCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acidHCID 89815259HCID 89815259, compound2×

Product 1

HCID 71737064HCID 71737064, compound

Procedure

The title compound was prepared in a manner analogous to Example 1, except that (2-methoxy-4-(trifluoromethyl)phenyl)boronic acid was used in place of (2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid and 5-chloro-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydro-2,6-naphthyridine-2(1H)-sulfonamide (Intermediate V) was used in place of 5-bromo-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide. [M+H]+=472.0 1H NMR (400 MHz, Acetone-d6) δ ppm: 8.41 (d, J=5.1 Hz, 1H), 8.25 (s, 1H), 7.35-7.44 (m, 3H), 7.20 (d, J=5.1 Hz, 1H), 4.26-4.51 (m, 2H), 3.89 (s, 3H), 3.43-3.56 (m, 1H), 3.15-3.26 (m, 1H), 2.82-2.93 (m., 1H), 2.40-2.56 (m, 1H)

Sources & evidence

ORD record
ord-72be7234806e483d8f5b00d190028bbe
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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