Sodium hydride → HCID 89462964, compound

HRID 1473181Notes

Reaction equation

[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]1[C:15]([N:17]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH3:18])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[C:9]2[C:15](=[O:16])[N:17]([CH3:18])[CH:19]([C:20]([O:22][CH3:23])=[O:21])[C:13](=[NH:14])[C:10]=2[CH:11]=[CH:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

An ice cold solution of methyl 2-(1-benzyl-3-cyano-N-methyl-1H-pyrrole-2-carboxamido)acetate (9.2 g, 29.6 mmol) in Tetrahydrofuran (THF) (100 mL) was treated with NaH, 60% dispersion in mineral oil, (1.536 g, 38.4 mmol) and the mixture was stirred at 0° C. for 30 minutes, then allowed to warm to room temperature and stirred an additional 2 hours at ambient temperature. The mixture was quenched with saturated NH4Cl solution at 0° C. and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford methyl 1-benzyl-4-imino-6-methyl-7-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (9.0 g, 28.9 mmol, 98% yield) as a pale yellow solid which was used in the next step without any further purification. 1H NMR (400 MHz, DMSO-d6) ppm 7.42-7.51 (m, 1H) 7.18-7.36 (m, 5H) 6.78-6.89 (m, 1H) 6.39-6.54 (m, 2H) 5.77 (s, 2H) 3.78 (s, 3H) 3.38 (s, 3H); LCMS (m/z) ES+=312 (M+1).

Workup

temperatureto warm to room temperature
stirringstirred an additional 2 hours at ambient temperature
customThe mixture was quenched with saturated NH4Cl solution at 0° C.
extractionextracted with ethyl acetate
washThe combined extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-b8a4af1090f745189ffd4552b27eb724
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012642B2

Reaction notes

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