Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester → 2-Methanesulfonyl-5-(4-{5-methyl-4-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-oxazol-2-yl}-phenyl)-pyridine

HRID 1445832Notes

Reaction equation

HRID 1445832 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14]OS(C)(=O)=O)[N:12]=2)=[CH:4][CH:3]=1.CC1O[C:25]([C:27]2[CH:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=CC=2)=[N:24]C=1CCO.[CH3:45][S:46]([C:49]1[CH:54]=[CH:53][C:52](I)=[CH:51][N:50]=1)(=[O:48])=[O:47]>>[CH3:45][S:46]([C:49]1[CH:54]=[CH:53][C:52]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14][N:24]4[CH2:25][CH2:27][CH2:32][C@H:31]4[CH3:30])[N:12]=3)=[CH:6][CH:7]=2)=[CH:51][N:50]=1)(=[O:48])=[O:47]

Participants

4

Reactant 3

HCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl esterHCID 589514312-{5-Methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-oxazol-4-yl}-ethanol2×HCID 589514522-Methanesulfonyl-5-iodo-pyridine2×

Product 1

HCID 116332542-Methanesulfonyl-5-(4-{5-methyl-4-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-oxazol-2-yl}-phenyl)-pyridine

Procedure

The titled compound is prepared substantially in accordance with the procedures of Example 4, Intermediate 13, and Example 75 using 2-{5-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-oxazol-4-yl}-ethanol (see Intermediate 3) and 2-methanesulfonyl-5-iodo-pyridine (see Intermediate 33). MS (m/e): 426.3 (M+1)

Sources & evidence

ORD record
ord-b99cfd7a6ff745ddbb131f1f6dd86f26
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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