2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 68548075, compound

HRID 219631Notes

Reaction equation

HRID 219631 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:16][CH2:15][CH2:14][C@@:13]([CH2:23][C:24]([CH3:26])=[CH2:25])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][N:31]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:28][O:29][C:30]1[CH:35]=[C:34]([C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]3[CH2:16][CH2:15][CH2:14][C@@:13]([CH2:23][C:24]([CH3:26])=[CH2:25])([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[O:12][C:11]3=[O:27])[CH3:9])=[CH:6][CH:7]=2)[CH:33]=[CH:32][N:31]=1

Participants

4

Reactant 2

HCID 447548622-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59190388HCID 59190388, compound

Product 1

HCID 68548075HCID 68548075, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

(R)-3-((S)-1-(4-(2-methoxypyridin-4-yl)phenyl)ethyl)-7-(2-methylallyl)-7-phenyl-1,3-oxazepan-2-one was prepared from (R)-3-((S)-1-(4-bromophenyl)ethyl)-7-(2-methylallyl)-7-phenyl-1,3-oxazepan-2-one and 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine following conditions analogous to those described in Example 6 using PdCl2(dppf) as catalyst. tR=2.28 min, m/z 457 (M+1). 1H NMR (CD3OD) δ 8.13 (m, 2H), 7.83 (d, 1H), 7.71 (d, 2H), 7.49 (t, 3H), 7.33 (t, 2H), 7.24 (m, 2H), 7.06 (d, 1H), 5.41 (q, 1H), 4.56 (s, 1H), 3.85 (d, 3H), 3.17-2.99 (m, 2H), 2.39 (dt, 1H), 2.09 (m, 1H), 1.45 (s, 3H), 1.38 (d, 3H).

Sources & evidence

ORD record
ord-380d4f84cc1947e9ac1d0d9541f84347
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Reaction notes

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