(2,4-Dichlorophenyl)boronic acid → HCID 60088309, compound

HRID 1836601Notes

Reaction equation

HRID 1836601 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:14]=[C:15]2[C:28]3[N:19]([CH2:20][C@@H:21]4[C@H:26]([C:27]=3[CH:29]=1)[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[CH2:18][CH2:17][CH2:16]2>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]2[C:28]3[N:19]([CH2:20][C@@H:21]4[C@H:26]([C:27]=3[CH:29]=1)[CH2:25][NH:24][CH2:23][CH2:22]4)[CH2:18][CH2:17][CH2:16]2

Participants

3

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 131724556HCID 131724556, compound

Product 1

HCID 60088309HCID 60088309, compound

Procedure

Using 2,4-dichlorophenylboronic acid and following the procedures described in EXAMPLE 20, (±)-cis tert-butyl 2-bromo-5,6,8,8a,9,10,12,12a-octahydro-4H,11H-quino[1,8-bc]-2,6-naphthyridine-11-carboxylate from EXAMPLE 127, Part F was converted into the title compound of EXAMPLE 128. 1H NMR (CDCl3) δ: 7.44 (d, 1H, J=1.6 Hz), 7.27-7.18 (m, 2H), 6.94 (B, 1H), 6.81 (s, 1H), 3.96 (dd, 1H, J=11.5, 3.1 Hz), 3.51-3.43 (m, 1H), 3.30-3.20 (m, 2H), 3.13 (d, 2H, J=7.3 Hz), 2.98-2.85 (m, 2H), 2.84-2.73 (m, 2H), 2.08-1.88 (m, 4H), 1.71-1.60 (m, 1H), 0.90-0.80 (m, 1H). LRMS (ES)+: 373.3 (M+H)+.

Sources & evidence

ORD record
ord-cef82460b07d4b6aa63c586115f5dbc0
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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