Dimethylformamide → HCID 11554931, compound

HRID 2220668Notes

Reaction equation

HRID 2220668 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2C=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=2C=O)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36]([OH:42])([C:38](F)(F)F)=[O:37].[H-].[Na+].C(Br)C1C=CC=CC=1.C[N:54](C=O)C>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17](=[NH:54])[NH2:18])[CH:15]=2)[C:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[C:38]([C:36]([OH:42])=[O:37])=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 87731314HCID 87731314, compound

Product 1

HCID 11554931HCID 11554931, compoundYield 83%

Conditions

Temperature
0 °C

Procedure

Part A. 1-benzyl-3-(2′-formyl-4′-methoxy-biphenyl-2-ylmethyl)-1H-indole-6-carbonitrile: The compound of Example 1, Part B (0.1 g, 0.27 mmol) was dissolved in 2 mL DMF and cooled to 0° C. in an ice bath. To the cold solution was added sodium hydride (60% in oil, 12 mg, 0.30 mmol), and the mixture was stirred for 10-15 min followed by addition of benzyl bromide (0.036 ml, 0.30 mmol). The reactoin was then stirred overnight at rt. Work-up and chromatography provided the N-benzylindole (0.1 g, 83%) as a white solid. LRMS m/z 457.1 (M+H)+.

Workup

  1. stirringThe reactoin was then stirred overnight at rt

Sources & evidence

ORD record
ord-ca77cb741a7044bb99ba35866ef023bc
Source dataset
uspto-grants-2008_08
Patent number
US07417063B2

Reaction notes

Loading…