Quinoline-3-boronic acid → methyl (2S)-4-methyl-2-{[(R)-phenyl(4-quinolin-3-ylphenyl)methyl]oxy}pentanoate

HRID 1180431Notes

Reaction equation

HRID 1180431 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:9][C@@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27](B(O)O)[CH:26]=1>>[CH3:17][CH:16]([CH3:18])[CH2:15][C@H:10]([O:9][C@H:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5]1[CH:6]=[CH:7][C:2]([C:27]2[CH:26]=[N:25][C:34]3[C:29]([CH:28]=2)=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:3][CH:4]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

3

Reactant 2

HCID 2734663Quinoline-3-boronic acidHCID 69469636methyl(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoate

Product 1

HCID 86605399methyl (2S)-4-methyl-2-{[(R)-phenyl(4-quinolin-3-ylphenyl)methyl]oxy}pentanoate

Procedure

Using the same procedure as described for example 36 step 2, methyl (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoate (2.05 g, 5.25 mmol) and 3-quinolineboronic acid (1.0 g, 5.78 mmol) were coupled to give the title compound as an oil.

Sources & evidence

ORD record
ord-d835a012d4f04e98abc1db7db3a206c4
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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