Methyl iodide → HCID 22253373, compound

HRID 1612383Notes

Reaction equation

[CH2:1]([CH:3]([N:6]1[C:14]2[CH:13]=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[C:9]=2[CH2:8][C:7]1=[O:26])[CH2:4][CH3:5])[CH3:2].[Li][CH2:28]CCC.CCCCCC.CI>C1COCC1>[CH2:1]([CH:3]([N:6]1[C:14]2[CH:13]=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[C:9]=2[CH:8]([CH3:28])[C:7]1=[O:26])[CH2:4][CH3:5])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a −78° C. solution of 1-(1-ethyl-propyl)-6-methyl-4-(2,4,6-trimethyl-phenoxy)-1,3-dihydro-pyrrolo[3,2-c]pyridin-2-one (352 mg, 1.0 mmol) in 2 ml of dry THF was added 2.5M BuLi in hexane (0.4 mmol, 1.0 mmol). The resulting mixture was stirred at −78° C. for 30 min, then transferred to a −78° C. solution of methyl iodide (3 ml) in 3 ml of dry THF. The resulting mixture was stirred at −78° C. for 1 hour, quenched with saturated ammonium chloride, extracted with ethyl acetate. The organic layer was dried and concentrated to give a clear oil which was purified through silica gel column chromatography using hexane to 10% ethyl acetate in hexane as eluent to give the title compound as tan solid 214 mg (68%). 1H NMR (CDCl3) δ 6.88 (s,2H), 6.47(s,1H), 4.1(m,1H), 3.56(q,1H), 2.30(s,3H), 2.26(s,3H), 2.07(s,6H), 1.7–2.0(m,4H), 1.60(d,3H), 0.86(t,6H) ppm.

Workup

customtransferred to a −78° C.
stirringThe resulting mixture was stirred at −78° C. for 1 hour
customquenched with saturated ammonium chloride
extractionextracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated
customto give a clear oil which
customwas purified through silica gel column chromatography

Sources & evidence

ORD record: ord-a2755bbe238a4c5c9498cef6e690aa6d
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992188B1

Reaction notes

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