Diethyl Ether → (1-Benzyl-5-bromo-1H-indol-2-yl)methanol

HRID 346840Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].CCOCC>C1COCC1>[Br:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([CH2:4][OH:3])=[CH:14]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6.7 g (19 mmol) of 5-bromo-1-(benzyl)indole-2-carboxylic acid ethyl ester in 25 mL of anhydrous THF at 0° C. were added portionwise 1.42 g (37 mmol) of LiAlH4 and the resulting mixture was stirred at 0° C. for 2 h. After addition of a saturated aqueous solution of NH4Cl and Et2O, the phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 5.8 g (ca 19 mmol) of [5-bromo-1-(benzyl)-1H-indol-2-yl]-methanol, that was dissolved in 30 mL of CH2Cl2 and treated at 0° C. with 4.75 mL (28 mmol) of DIPEA 7.5 mL (28 mmol) of TIPSOTf. The mixture was stirred at RT for 1 h and added to saturated aqueous NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 7.3 g (81%) of 5-bromo-1-(benzyl)-2-triisopropylsilanyloxymethyl-1H-indole, off-white solid, MS: 473 (MH+).

Workup

customthe phases were separated
extractionthe aqueous one was extracted with Et2O
dry with materialThe combined organic phases were dried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-227a897fc16942fba4042d558ebc8ef4
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173048B2

Reaction notes

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