Dimethylformamide → HCID 86637862, compound

HRID 1518261Notes

Reaction equation

[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[CH2:28][O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C.[CH2:45](Br)[C:46]#[CH:47]>CCOCC>[CH3:19][O:18][C:16]([C:12]1[CH:11]=[C:10]2[C:15]([C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:8]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[CH2:28][O:29][Si:30]([CH:31]([CH3:32])[CH3:33])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[N:9]2[CH2:47][C:46]#[CH:45])=[CH:14][CH:13]=1)=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice cooled solution of methyl-3-cyclohexyl-2-(4-methoxy-2-{[(triisopropylsilyl) oxy]methyl}phenyl)-1H-indole-6-carboxylate (Example 12, Step 4) in DMF (0.13 M) 60% NaH (2 eq.) was added. After 20 min. propargyl bromide (solution 80% in toluene) (1.5 eq.) was added and the mixture stirred at 0° C. for 1 h, diluted with Et2O, washed with sat aq. NH4Cl and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was subjected to flash chromatography (PE:EtOAc, 20:1). After evaporation of the solvents the product was obtained as a white solid (96%). MS (ES+): 588.7 (M+H+).

Workup

washwashed
dry with materialThe organic phase was dried over Na2SO4
customevaporated in vacuo
customAfter evaporation of the solvents the product

Sources & evidence

ORD record: ord-1bfb1ba4500e41a0a60bf8c66ea6c3af
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232390B2

Reaction notes

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