Sodium hydride → Benzyl {(S)-2-[6-(4-benzyloxyphenoxy)pyridin-3-yloxy]-1-methylethyl}carbamate

HRID 1260544Notes

Reaction equation

HRID 1260544 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]2[N:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:24][C@@H:25]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:26].[H-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]2[N:19]=[CH:18][C:17]([O:20][CH2:26][C@@H:25]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:24])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 670715476-(4-Benzyloxyphenoxy)pyridin-3-olHCID 71301833(S)-Benzyl (1-bromopropan-2-yl)carbamate

Product 1

HCID 86761884Benzyl {(S)-2-[6-(4-benzyloxyphenoxy)pyridin-3-yloxy]-1-methylethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(4-Benzyloxyphenoxy)pyridin-3-ol (250 mg, 0.85 mmol) and benzyl ((S)-2-bromo-1-methylethyl)carbamate (232 mg, 0.85 mmol) were reacted with sodium hydride in DMF in analogy to example 1a. Yield: 118 mg (29%), M+H+: 485.11.

Sources & evidence

ORD record
ord-39a456377ac14238b7ca8c9e5785e9a0
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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