HCID 58636705, compound → HCID 58636748, compound

HRID 1158974Notes

Reaction equation

HRID 1158974 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[C:6]([O:10][C:11](=[O:41])[N:12]([CH2:21][C:22]1[CH:23]=[N:24][C:25]([CH3:40])=[C:26]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=2)[C:27]=1[CH:28]=[O:29])[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)([CH3:9])([CH3:8])[CH3:7]>>[C:6]([O:10][C:11](=[O:41])[N:12]([CH2:21][C:22]1[CH:23]=[N:24][C:25]([CH3:40])=[C:26]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=2)[C:27]=1[CH:28]([CH:1]1[CH2:3][CH2:2]1)[OH:29])[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 58636705HCID 58636705, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 58636748HCID 58636748, compoundYield 62.1%

Procedure

The addition of cyclopropyl magnesium bromide (2.8 mL, 0.5 M, 1.4 mmol) to 5-(3-cyano-benzyloxy)-4-formyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (109) (474 mg, 0.9 mmol), was carried out as described in Example 104, gave [5-(3-cyano-benzyloxy)-4-(cyclopropyl-hydroxy-methyl)-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (117) (293 mg, 57% yield).

Sources & evidence

ORD record
ord-7cb1f4f44f674cfa82c60be979aeac07
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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