Ammonium Chloride → 1-(3-cyano-benzoyl)-3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile

HRID 1661567Notes

Reaction equation

HRID 1661567 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[N:22])[CH:19]=2)[NH:14][C:13]=1[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.[C:29]([C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](Cl)=[O:35])#[N:30].[Cl-].[NH4+]>C1COCC1>[C:29]([C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([N:14]1[C:15]2[C:20](=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[C:12]([CH3:11])=[C:13]1[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[O:35])#[N:30]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 3084833-Cyanobenzoyl chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 445541323-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile

Product 1

HCID 582155961-(3-cyano-benzoyl)-3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

KHMDS (0.5 M in toluene, 1.46 mL, 0.73 mmol) is added to a solution of 3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile (Example 6, 122 mg, 0.480 mmol) in THF (10 mL) at room temperature. After 5 min, 3-cyanobenzoyl chloride (178 mg, 1.08 mmol) is added. The mixture is stirred under N2 for 1 h, whereupon aqueous ammonium chloride (0.5 mL) is added. The solvents are removed in vacuo and the residue is purified by Xbridge RP18 with a 0.1% aqueous ammonium hydroxide in acetonitrile gradient to give 1-(3-cyano-benzoyl)-3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile. 1H NMR (400 MHz, CDCl3) δ ppm 2.35 (s, 3H), 7.37-7.44 (m, 1H), 7.47-7.52 (m, 1H), 7.60-7.64 (m, 1H), 7.68-7.83 (m, 5H), 8.01 (d, J=1.5 Hz, 1H), 8.51 (d, J=4.5 Hz, 1H), 8.53 (s, 1H). HRMS (ESI) m/z 363.1247 [(M+H)+ Calcd for C23H15N4O: 363.1246].

Workup

  1. additionis added
  2. customThe solvents are removed in vacuo
  3. customthe residue is purified by Xbridge RP18 with a 0.1% aqueous ammonium hydroxide in acetonitrile gradient

Sources & evidence

ORD record
ord-0948da1752554b3e89b9fd04d001cfa4
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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