Tetrahydrofuran → 1-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile

HRID 2097099Notes

Reaction equation

C([Li])(C)(C)C.C1C[O:9][CH2:8]C1.[CH2:11]([O:13][CH:14]([O:26][CH2:27][CH3:28])[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]#[N:25])=[CH:16]1)[CH3:12]>CN(C=O)C>[CH2:11]([O:13][CH:14]([O:26][CH2:27][CH3:28])[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]#[N:25])=[C:16]1[CH:8]=[O:9])[CH3:12]

Participants

Conditions

Temperature: 10 °C

Procedure

tert-Butyl lithium (18.1 mL, 31 mmol, 1.7M in pentane) was added to a THF (100 mL) solution of 1-diethoxymethyl-1H-indole-3-carbonitrile (6.83 g, 28 mmol) at −78° C. The mixture was warmed to 10° C., stirred for 30 min at this temperature, cooled to −78° C. and heated with DMF (20 mL). The mixture was warmed to 10° C., stirred for 30 min at this temperature, cooled to −78° C. and quenched with a saturated aqueous solution of NaHCO3. The resulting mixture was treated with ether (200 mL); the organic layer was washed with water and brine, dried and evaporated to dryness. NMR (300 MHz, CDCl3, 8): 10.24 (s, 1H), 8.10 (d, J=7.7 Hz, 1H), 7.91 (d, J=7.7 Hz, 1H), 7.53 (t, J=7.7 Hz, 1H), 7.43 (t, J=7.5 Hz, 1H), 7.34 (s, 1H), 3.80 (m, 2H), 3.52 (m, 2H), 1.26 (t, J=6.4 Hz, 1H).

Workup

temperaturecooled to −78° C.
temperatureThe mixture was warmed to 10° C.
stirringstirred for 30 min at this temperature
temperaturecooled to −78° C.
customquenched with a saturated aqueous solution of NaHCO3
additionThe resulting mixture was treated with ether (200 mL)
washthe organic layer was washed with water and brine
customdried
customevaporated to dryness

Sources & evidence

ORD record: ord-a041e2facdf34591a7fe50680f85b01c
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450307B2

Reaction notes

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