Ethyl 5-cyanoindole-2-carboxylate → HCID 67095796, compound

HRID 1866234Notes

Reaction equation

HRID 1866234 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]#[N:16])=[CH:10][CH:9]=2)=O)C.[NH3:17].CO>>[C:15]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([NH2:17])=[O:3])=[CH:14]2)#[N:16]

Participants

3

Reactant 2

HCID 4714953Ethyl 5-cyanoindole-2-carboxylateHCID 21705897Ammonia methanol

Product 1

HCID 67095796HCID 67095796, compoundYield 83.3%

Procedure

Treat 5-cyano-1H-indole-2-carboxylic acid ethyl ester, 3a (m=0, 1.0 g, 4.67 mmol) with 7 N NH3/MeOH as described in General Procedure IV to afford the title compound as an ivory colored solid (720 mg, 83.3%): mp>300° C.; 1H NMR (DMSO-d6) δ 12.0 (brs, 1H), 8.21 (s, 1H), 8.14 (brs, 1H), 7.51 (m, 3H), 7.25 (s, 1H); tlc (10% MeOH/CH2Cl2) Rf=0.40, m/z obs=186 (M+1).

Sources & evidence

ORD record
ord-d63bc24077fa45948197910651ea447b
Source dataset
uspto-grants-2009_12
Patent number
US07629376B2

Reaction notes

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