N-Methoxy-N-methylbenzamide → 2-Phenyl-1H-pyrrolo[3,2-C]pyridine

HRID 1490240Notes

Reaction equation

HRID 1490240 reaction equation
C(O[C:6]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[CH3:15])=O)(C)(C)C.C([Li])(C)(C)C.CON(C)C(=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:25]1([C:6]2[NH:8][C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[CH:15]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 569575N-Methoxy-N-methylbenzamideHCID 15273533tert-butyl N-(3-methylpyridin-4-yl)carbamateHCID 178418306HCID 178418306, compound

Product 1

HCID 152108622-Phenyl-1H-pyrrolo[3,2-C]pyridine

Procedure

4-tert-Butoxycarbonylamino-3-methylpyridine (Example 11a, 1.0 g, 4.8 mmol) was dilithiated with t-butyllithium and treated with N-methoxy-N-methylbenzamide (0.95 g, 5.76 mmol) as described previously. The crude product was purified by trituration with ethyl acetate to afford the title compound as a pale beige solid; yield: 0.59 g (63%); mp 276°-278°C.[Lit. mp 282°-283° C.].

Workup

  1. customThe crude product was purified by trituration with ethyl acetate

Sources & evidence

ORD record
ord-ba3c977682f5489481c2938aa8bd8000
Source dataset
uspto-grants-1997_10
Patent number
US05681959

Reaction notes

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