Dimethylformamide → HCID 66672924, compound

HRID 422250Notes

Reaction equation

HRID 422250 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:30])[NH:9][CH2:10][CH:11]1[C:20]2[C:15](=[C:16]([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][N:23]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)([CH3:6])([CH3:5])[CH3:4].CN(C=O)C.Br[CH2:37][CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41]>O>[C:3]([O:7][C:8](=[O:30])[N:9]([CH2:10][CH:11]1[C:20]2[C:15](=[C:16]([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][N:23]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)[CH2:37][CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 69385Pentane, 1-bromo-4-methyl-HCID 59750689HCID 59750689, compound2×

Product 1

HCID 66672924HCID 66672924, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add NaH (60% oil suspension, 30 mg, 0.750 mmol) to a solution of [5-(5-cyanopyridin-2-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl ester (Intermediate 22, 189 mg, 0.500 mmol) and DMF (5 ml) stirring at ambient temperature under nitrogen. After 20 minutes, add 1-bromo-4-methylpentane (247 mg, 1.50 mmol) and beat the mixture at 60° C. overnight. After cooling, pour the mixture into water and extract with EtOAc (2×). Wash the extract with water and brine before drying ((MgSO4) and concentrating. Purify on silica gel (20% EtOAc/Hexane) to obtain 111 mg of [5-(5-cyano-pyridin-2-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-(4-methyl-pentyl)carbamic acid tert-butyl ester as a colorless glass.

Workup

  1. temperatureAfter cooling
  2. extractionextract with EtOAc (2×)
  3. washWash the
  4. extractionextract with water and brine
  5. dry with materialbefore drying ((MgSO4)
  6. concentrationconcentrating
  7. customPurify on silica gel (20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-440241766f5644e5875cd07c9aa23a69
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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