ethyl 5-cyano-6-methoxy-1H-indole-2-carboxylate → ethyl 5-[amino(hydroxyimino)methyl]-6-methoxy-1H-indole-2-carboxylate

HRID 400731Notes

Reaction equation

HRID 400731 reaction equation
[OH:1][N:2]=C(C1C=CC2NC=NC=2C=1)N.[C:14]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[NH:21][C:20]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:19]2)#[N:15]>>[NH2:15][C:14](=[N:2][OH:1])[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[NH:21][C:20]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:19]2

Participants

3

Reactant 2

HCID 67401331ethyl 5-cyano-6-methoxy-1H-indole-2-carboxylateHCID 178513241N'-hydroxy-3H-benzimidazole-5-carboximidamide

Product 1

HCID 76787425ethyl 5-[amino(hydroxyimino)methyl]-6-methoxy-1H-indole-2-carboxylate

Procedure

The title compound was prepared following procedure described for Intermediate 1, step 2, but starting from ethyl 5-cyano-6-methoxy-1H-indole-2-carboxylate obtained in step 1 (120 mg; 0.49 mmol) as a beige solid (135 mg, 99%). 1H NMR (DMSO-d5) δ 9.25 (s, 1H), 7.60 (s, 1H), 7.11 (s, 1H), 6.90 (s, 1H), 5.53 (bs, 2H), 4.31 (q, J=7 Hz, 2H), 3.80 (s, 3H), 1.32 (t, J=7 Hz, 3H).

Sources & evidence

ORD record
ord-90e2d9327ce9446d99bdadfd86cadbe0
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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