Sodium hydride → HCID 57434483, compound

HRID 1694387Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([F:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[CH:5]=[C:6]2[C:10]=1[N:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=1)[CH:8]=[CH:7]2

Participants

Conditions

Temperature: -10 °C

Procedure

7-bromo-5-fluoro-1H-indole (900 mg, 4.20 mmol) and 1-(bromomethyl)-4-(trifluoromethyl)benzene (1.6 g, 6.7 mmol) were dissolved in DMF (20 ml). The mixture was cooled to −10° C. and NaH (185 mg, 4.6 mmol) was added portion wise over 5 min. The mixture was stirred for 1 hour at this temperature. Quenched with NH4Cl (½ sat.) and 1N HCl. The mixture was diluted with water and the aqueous phase was extracted 3× with ether. The combined organic layers were washed with 3× water, 1× brine and dried over MgSO4. The product was purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 7.70 (m, 3H), 7.45 (dd, 1H), 7.25 (dd, 1H), 7.10 (d, 2H), 6.65 (d, 1H), 5.90 (s, 2H).

Workup

customQuenched with NH4Cl (½ sat.) and 1N HCl
additionThe mixture was diluted with water
extractionthe aqueous phase was extracted 3× with ether
washThe combined organic layers were washed with 3× water, 1× brine
dry with materialdried over MgSO4
customThe product was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-6876550423e549cf9902ca0d92337acb
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158671B2

Reaction notes

Loading…